Category: 77326-36-4

Electric Literature of 77326-36-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under argon, 2-amino-6-fluorobenzonitrile (300 mg, 2.20 mmol) was dissolved in pyridine (3.6 ml, 44 mmol), 4-dimethylaminopyridine (2.69 mg, 22.0 muiotaetaomicron) and 3-Chlorobenzoylchlorid (501 mg, 2.86 mmol) were added and the mixture was stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate, washed with water and brine, and dried over magnesium sulfate. Concentration in vacuo and purification by preparative HPLC afforded the title compound. The obtained amount was 401 mg (100% Purity, 66 % of theory). LC-MS (Method 1): Rt = 0.97 min; MS (ESIPos): m/z = 275 [M+H]+

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUSS, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; (308 pag.)WO2016/173948; (2016); A1;,
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Application of 77326-36-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2: Methyl- (2-cyano-3-methoxy-phenyl) sulfonamide; 2.1 : 2-Amino-6-methoxy-benzonitrile A solution of 70 g (0.5 mol) of 2-amino-6-fluoro-benzonitrile (prepared, e. g. according to US 4,504, 660) in 250 ml of N, N-dimethylformamide was initially charged and a solu- tion of 30.6 g (0.55 mol) sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours under stirring. The completion of the reaction was monitored by TLC. Additional 25 g of so- dium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for additional 4 hours while stirring. The reaction mixture was concentrated under re- duced pressure, the resulting residue was triturated with water, sucked off and the ob- tained solids were dissolved in ethyl acetate. The resulting solution was concentrated in vacuo. The obtained residue was triturated with petroleum ether and sucked off to afford 48 g (63% of theory) of a brownish solid having a melting point of 143-146C.

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2005/35486; (2005); A1;,
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Electric Literature of 77326-36-4,Some common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, molecular formula is C7H5FN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Sodium hydride (0.154 g, 3.85 mmol, 1.5 equiv) was added to a mixture of 2-amino-6-fluorobenzonitrile (0.524 g, 3.85 mmol, 1.5 equiv) and 2-methyl-2-((5-methylpyrimidin-2-yl)amino)propan-1-ol (Example 1b, 0.465 g,2.56 mmol, 1 equiv) in anhydrous THF (25 mL) under nitrogen. The reaction mixture was stirred for 10 minutes at room temperature and refluxed for 21 h. The reaction mixture was concentrated and the residue was purified by chromatography on a silica(50% EtOAc in Hexanes gradient) to provide the title compound (611 mg, 80% yield), MS 298 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-fluorobenzonitrile, its application will become more common.

Reference:
Patent; FIRMENICH INCORPORATED; FOTSING, Joseph, R.; TACHDJIAN, Catherine; SERVANT, Guy; CHING, Brett, Weylan; DAVIS, Timothy; (94 pag.)WO2020/33420; (2020); A1;,
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Electric Literature of 77326-36-4, These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2-ethoxy-N-(trans-4-hydroxycyclohexyl)acetamide (20.10 g, 99.87 mmol) in anhydrous 1,4-dioxane (800 mL), was added portion-wise sodium hydride (4.33 g, 108.25 mmol, 60% in mineral oil) at room temperature under nitrogen. The mixture was stirred for 1 h at room temperature, and then a solution of 2-amino-6-fluorobenzonitrile (11.34 g, 83.30 mmol) in anhydrous 1,4-dioxane (200 mL) was added drop-wise. The reaction mixture was heated at 90 oC over 72 h, cooled to room temperature, concentrated under reduced pressure, ice water (150 mL) was carefully added and extracted with EtOAc (5 x 200 mL). The combined extract was washed with brine, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography (35% to 65% EtOAc in hexanes) to afford 18.98 g (72%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.18 (t, J = 8.2 Hz, 1H), 6.44 (d, J = 8.2 Hz, 1H), 6.29 (d, J = 8.3 Hz, 1H), 6.21 (d, J = 8.3 Hz, 1H), 4.39 (br s, 2H), 4.31-4.21 (m, 1H), 4.91 (s, 2H), 3.97-3.84 (m, 1H), 3.57 (q, J = 7.0 Hz, 2H), 2.19-2.05 (m, 4H), 1.78-1.63 (m, 2H), 1.44-1.29 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H). MS 318 (MH+).

The synthetic route of 77326-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYX, INC.; PETROVIC, Goran; FOTSING, Joseph; SERVANT, Guy; TACHDJIAN, Catherine; KARANEWSKY, Donald; VONG, Binh; BOREN, Brant, Clayton; CHEN, Qing; ZHANG, Hong; CHING, Brett, Weylan; LAPERA, Stephanie; (99 pag.)WO2016/73251; (2016); A1;,
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These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 2-Amino-6-fluorobenzonitrile

[6-(4-Methyl-piperazin-1-yl)-1H-benzimidazol-2-yl]-acetic acid ethyl ester (250 g, 820 mmol) (dried with ethanol as described above) was dissolved in THF (3800 mL) in a 5000 mL flask fitted with a condenser, mechanical stirrer, temperature probe, and purged with argon. 2-Amino-6-fluoro-benzonitrile (95.3 g, 700 mmol) was added to the solution, and the internal temperature was raised to 40 C. When all the solids had dissolved and the solution temperature had reached 40 C., solid KHMDS (376.2 g, 1890 mmol) was added over a period of 5 minutes. When addition of the potassium base was complete, a heterogeneous yellow solution was obtained, and the internal temperature had risen to 62 C. After a period of 60 minutes, the internal temperature decreased back to 40 C., and the reaction was determined to be complete by HPLC (no starting material or uncyclized intermediate was present). The thick reaction mixture was then quenched by pouring i into H2O (6000 mL) and stirring the resulting mixture until it had reached room temperature. The mixture was then filtered, and the filter pad was washed with water (1000 mL 2×). The bright yellow solid was placed in a drying tray and dried in a vacuum oven at 50 C. overnight providing 155.3 g (47.9%) of the desired 4-amino-5-fluoro-3-[6-(4-methyl-piperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one.Procedure B A 5000 mL 4-neck jacketed flask was equipped with a distillation apparatus, a temperature probe, a N2 gas inlet, an addition funnel, and a mechanical stirrer. [6-(4-Methyl-piperazin-1-yl)-1H-benzimidazol-2-yl]-acetic acid ethyl ester (173.0 g, 570 mmol) was charged into the reactor, and the reactor was purged with N2 for 15 minutes. Dry THF (2600 mL) was then charged into the flask with stirring. After all the solid had dissolved, solvent was removed by distillation (vacuum or atmospheric (the higher temperature helps to remove the water) using heat as necessary. After 1000 mL of solvent had been removed, distillation was stopped and the reaction was purged with N2. 1000 mL of dry THF was then added to the reaction vessel, and when all solid was dissolved, distillation (vacuum or atmospheric) was again conducted until another 1000 mL of solvent had been removed. This process of adding dry THF and solvent removal was repeated at least 4 times (on the 4th distillation, 60% of the solvent is removed instead of just 40% as in the first 3 distillations) after which a 1 mL sample was removed for Karl Fischer analysis to determine water content. If the analysis showed that the sample contained less than 0.20% water, then reaction was continued as described in the next paragraph. However, if the analysis showed more than 0.20% water, then the drying process described above was continued until a water content of less than 0.20% was achieved. After a water content of less than or about 0.20% was achieved using the procedure described in the previous paragraph, the distillation apparatus was replaced with a reflux condenser, and the reaction was charged with 2-amino-6-fluoro-benzonitrile (66.2 g, 470 mmol)(in some procedures 0.95 equivalents is used). The reaction was then heated to an internal temperature of 38-42 C. When the internal temperature had reached 38-42 C., KHMDS solution (1313 g, 1.32 mol, 20% KHMDS in THF) was added to the reaction via the addition funnel over a period of 5 minutes maintaining the internal temperature at about 38-50 C. during the addition. When addition of the potassium base was complete, the reaction was stirred for 3.5 to 4.5 hours (in some examples it was stirred for 30 to 60 minutes and the reaction may be complete within that time) while maintaining the internal temperature at from 38-42 C. A sample of the reaction was then removed and analyzed by HPLC. If the reaction was not complete, additional KHMDS solution was added to the flask over a period of 5 minutes and the reaction was stirred at 38-42 C. for 45-60 minutes (the amount of KHMDS solution added was determined by the following: If the IPC ratio is <3.50, then 125 mL was added; if 10.0IPC ratio 3.50, then 56 mL was added; if 20.0IPC ratio 10, then 30 mL was added. The IPC ratio is equal to the area corresponding to 4-amino-5-fluoro-3-[6-(4-methyl-piperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one) divided by the area corresponding to the uncyclized intermediate). Once the reaction was complete (IPC ratio >20), the reactor was cooled to an internal temperature of 25-30 C., and water (350 mL) was charged into the reactor over a period of 15 minutes while maintaining the internal temperature at 25-35 C. (in one alternative, the reaction is conducted at 40 C. and water is added within 5 minutes. The quicker quench reduces the amount of impurity that forms over time). The reflux condenser was then replaced with a distillation apparatus and solvent was removed by distillation (vacuum or atmospheric) using heat as required. After 1500 mL of solvent had been removed, distillation was disc…

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US2008/293738; (2008); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H5FN2

To a solution of 3-hydroxy-2,2-dimethyl-N-propy- lpropanamide (20.2 g, 0.127 mol) (Example 197d) in dry THF (500 mE) was carefully added NaH (60% in mineral oil, 7.64 g, 0.191 mol) in small portions at 0C. under nitrogen. The reaction mixture was then warmed to room temperature and stirred under nitrogen for 1 hr. To this solution was slowly added at room temperature 2-amino-6-fluorobenzo-nitrile (17.3 g, 0.127 mol) in THF (100 mE) and the reaction mixture refluxed overnight under nitrogen then cooled down to room temperature, quenched with brine, and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na2SO4, evaporated and the residue was crystallized from EtOAc/Hexane to give the compound as a white solid (16.5 g, 48%). MS 276 (MHj.

According to the analysis of related databases, 77326-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
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Related Products of 77326-36-4, These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

It was prepared as described for 8. Starting from freshly sublimed 2-amino-6-fluorobenzonitrile (918 mg, 6.75 mmol) in 1,2-dichloroethane (8 mL) and enone 7 (R9 = allyl) (800 mg, 4.50 mmol) in 1,2-dichloroethane (40 mL), and heating the reaction mixture under reflux for 16 h, a crude product (1.75 g) was obtained and subjected to column chromatography [silica gel (62 g), CH2Cl2/MeOH/25% aqueous NH4OH mixtures as eluent]. On elution with CH2Cl2/MeOH/25% aqueous NH4OH 99:1:0.05, huprine 11 (762 mg, 58% yield) was obtained as a beige solid.A solution of huprine 11 (762 mg, 2.59 mmol) in MeOH (6 mL) was treated with 1.81 N methanolic HCl (4.3 mL, 7.78 mmol) and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 15:2 (34 mL), 11·HCl was obtained as a light brown solid (570 mg), mp >300 C (dec.) (AcOEt/MeOH 15:2). IR (KBr) nu 3600-2400 (max at 3394, 3314, 3201, 3166, 3071, 3020, 2926, 2902, 2829, 2774, 2669, 2604, C-H, N-H, and N+-H st), 1640, 1593, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 1.98 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.05 (br d, J ? 17.5 Hz, 1H, 10-Hendo), 2.10 (dm, J = 12.5 Hz, 1H, 13-Hanti), 2.51 (ddm, J = 17.5 Hz, J’ = 5.5 Hz, 1H, 10-Hexo), 2.63 (d, J ? 7.0 Hz, 2H, 9-CH2-CHCH2), 2.83 (m, 1H, 7-H), 2.88 (ddd, J = 18.0 Hz, J’ = J = 2.0 Hz, 1H, 6-Hendo), 3.22 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.40 (m, 1H, 11-H), 4.86 (s, NH2 and NH+), 4.88-4.91 (complex signal, 2H, 9-CH2-CHCH2), 5.63 (dm, J = 7.0 Hz, 1H, 8-H), superimposed in part 5.65 (ddt, J = 17.0 Hz, J’ = 10.0 Hz, J = 7.0 Hz, 1H, 9-CH2-CHCH2), 7.34 (ddd, J = 14.0 Hz, J’ = 8.5 Hz, J = 1.0 Hz, 1H, 2-H), 7.57 (ddd, J = 8.5 Hz, J’ = J = 1.0 Hz, 1H, 4-H), 7.83 (ddd, J = J’ = 8.5 Hz, J = 6.0 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 27.2 (CH, C11), 28.1 (CH, C7), 29.3 (CH2, C13), 34.0 (CH2, C10), 35.9 (CH2, C6), 42.5 (CH2, 9-CH2-CHCH2), 107.4 (C, d, J = 12.1 Hz, C12a), 112.2 (CH, d, J = 23.0 Hz, C2), 115.8 (C, C11a), 116.3 (CH, C4), 116.4 (CH2, 9-CH2-CHCH2), 125.7 (CH, C8), 135.0 (CH, d, J = 11.5 Hz, C3), 137.2 (CH, 9-CH2-CHCH2), 137.3 (C, C9), 140.7 (C, C4a), 152.9 (C) and 155.4 (C) (C5a and C12), 161.2 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H19FN2·HCl (330.83): C, 68.98; H, 6.09; N, 8.47; Cl, 10.72. Found: C, 68.65; H, 6.20; N, 8.35; Cl, 11.14.

Statistics shows that 2-Amino-6-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 77326-36-4.

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H5FN2

General procedure: To the solution of anthranilonitrile S-1 (2.0 mmol) and Et3N (2.4 mmol) in 20 mL dry CH2Cl2 was added acryloyl chloride (2.2 mmol) at 0 C. The mixture was allowed to stir at room temperature. After completion of the reaction, the reaction was quenched with saturated NaHCO3 solution, then extracted with CH2Cl2, washed with brine, dried over MgSO4 and concentrated by evaporator affording amide S-2 without any further purification.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Yang, Tao; Zhou, Jia-Li; Li, Junpeng; Shen, Yuehai; Gao, Chuanzhu; Li, Ya-Min; Synthesis; vol. 50; 17; (2018); p. 3460 – 3466;,
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These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 77326-36-4

Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYS, INC.; US2011/245353; (2011); A1;,
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Related Products of 77326-36-4, The chemical industry reduces the impact on the environment during synthesis 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of amino alcohol (0.91 eq.) inanhydrous THF (5 ml) was added NaH as a 60% dispersion in oil (1.0 eq.). Themixture was stirred at 0 C for 30 min, at r.t. for another 30 min beforecooling down to 0 C again. 2-Amino-6-fluorobenzonitrile (1.0 eq.) was addedand the reaction was refluxed for 2 hours before cooling down to r.t. H2O(0.7 ml) was added and the solvents were evaporated in vacuo. The residue was purified by flash column chromatography.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Amino-6-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hensbergen, Albertus Wijnand; Mills, Vanessa R.; Collins, Ian; Jones, Alan M.; Tetrahedron Letters; vol. 56; 46; (2015); p. 6478 – 6483;,
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