Category: 77326-36-4

Synthetic Route of 77326-36-4, A common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, molecular formula is C7H5FN2, 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 (R)-1-(3-(hydroxymethyl)piperidin-1-yl)-3-methylbutan-1-one5 (Example 34c) (145 mg, 0.73 mmol) in THF (15 mL) was added NaH (44 mg, 1.09 mmol,60% dispersion in mineral oil) at 0 C. The reaction was warmed to room temperature andstirred for 15 minutes, at which time 2-amino-6-fluorobenzonitrile (109 mg, 0.80 mmol) wasadded. The mixture was heated at 80 C overnight, quenched with water, concentrated underreduced pressure to remove THF and extracted with EtOAc (3X). The combined extracts10 were dried over Na2S04, filtered, concentrated under reduced pressure and purified by flashchromatography on silica gel (EtOAc/hexanes). The residue was further purified by chiralHPLC (normal phase, ethanol/isopropanol/methanol/hexanes) to give the title compound as awhite solid (96 mg, 41% ). MS 316 (MH+).

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

Reference:
Patent; SENOMYX, INC.; TACHDJIAN, Catherine; KARANEWSKY, Donald; WERNER, Sara; DARMOHUSODO, Vincent; YAMAMOTO, Jeff; WO2014/25706; (2014); A1;,
Nitrile – Wikipedia,
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Related Products 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.

Add 2-amino-6-fluorobenzonitrile (136 mg, 1 mmol), benzyl alcohol (108 mg, 1 mmol),Fe (NO3) 3 · 9H2O (40.4 mg, 0.10 mmol), TEMPO (15.6 mg, 0.10 mmol),t-BuOK (224mg, 2equiv) and 2mL of toluene were sequentially added to a 25mL reaction tube, and the reaction mixture was reacted under reflux for 12h and cooled to room temperature;Ethyl acetate was added to dilute the reaction solution, and then washed three times with water, and then the organic phase was separated.After drying over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product;The crude product was purified by column chromatography with petroleum ether / ethyl acetate, yielding 78%.

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

Reference:
Patent; Nanjing University of Science and Technology; Li Bindong; Hu Yongke; (12 pag.)CN110357823; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

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;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 77326-36-4, Application In Synthesis of 2-Amino-6-fluorobenzonitrile

Example 134b 3-(3-amino-2-cyanophenoxy)-N-isopropyl-2,2-dimethylpropanamide To a solution of 3-hydroxy-N-isopropyl-2,2-dimethylpropanamide (Example 134c, 5.12 g, 32.15 mmol) in dry THF (100 mL) was added portion-wise NaH (60% in mineral oil, 1.41 g, 35.37 mmol) at 0 C. under nitrogen. The reaction mixture was stirred at 0 C. for about 30 minutes until bubbling ceased. 2-Amino-6-fluorobenzo-nitrile (4.38 g, 32.15 mmol) was added and the solution stirred at 80 C. overnight. The reaction mixture was quenched slowly with water at 0 C., and concentrated under reduced pressure. The residue was taken up in EtOAc and washed consecutively with brine and water, dried over Na2SO4 and concentrated. The residue was purified by re-crystallization from EtOAc/hexane to give the title compound as a white crystalline solid (4.4 g, 50%). 1H NMR (400 MHz, CDCl3) delta 1.18 (d, J=6.8 Hz, 6H), 1.32 (s, 6H), 3.94 (s, 2H), 4.04-4.12 (m, 1H), 4.43 (s, 2H), 5.98 (d, J=6.8 Hz, 1H), 6.21 (d, J=8.0 Hz, 1H), 6.32 (d, J=8.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H). MS 276 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

It was prepared as described for 8. Starting from 2-amino-6-fluorobenzonitrile (318 mg, 2.31 mmol) in 1,2-dichloroethane (25 mL) and enone 7 (R9 = i-Pr) (272 mg, 1.53 mmol) in 1,2-dichloroethane (15 mL), a crude product (383 mg) was obtained and subjected to column chromatography [silica gel (19 g), hexane/AcOEt/25% aqueous NH4OH mixtures as eluent]. On elution with hexane/AcOEt/25% aqueous NH4OH 98:2:0.1, huprine 10 (220 mg, 42% yield) was obtained as a beige solid.A solution of huprine 10 (220 mg, 0.74 mmol) in CH2Cl2 (15 mL) was filtered through a PTFE 0.45 mum filter, treated with 1.81 N methanolic solution of HCl (1.24 mL, 2.24 mmol), and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 30:1 (9.3 mL), 10·HCl (138 mg) was obtained as a beige solid, mp >300 C (dec.) (AcOEt/MeOH 30:1). IR (KBr) nu 3500-2500 (max at 3494, 3370, 3312, 3201, 3158, 3024, 2958, 2929, 2891, 2833, 2750, 2669, C-H, N-H, and N+-H st), 1640, 1595, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 0.87 (d, J = 7.0 Hz, 3H) and 0.89 (d, J = 7.0 Hz, 3 H) [9-CH(CH3)2], 1.97 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.02-2.12 [complex signal, 2H, 13-Hanti and 9-CH(CH3)2], superimposed in part 2.08 (br d, J = 17.5 Hz, 1H, 10-Hendo), 2.52 (br dd, J = 17.5 Hz, J’ = 5.0 Hz, 1H, 10-Hexo), 2.80 (m, 1H, 7-H), 2.86 (dm, J ? 18.0 Hz, 1H, 6-Hendo), 3.21 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.41 (m, 1H, 11-H), 4.85 (s, NH2 and NH+), 5.58 (dm, J = 5.0 Hz, 1H, 8-H), 7.34 (ddd, J = 13.5 Hz, J’ = 8.0 Hz, J = 1.0 Hz, 1H, 2-H), 7.56 (br d, J = 8.5 Hz, 1H, 4-H), 7.82 (dddm, J ? J’ ? 8.5 Hz, J = 5.5 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 21.4 (CH3) and 21.9 (CH3) [9-CH(CH3)2], 27.2 (CH, C11), 27.9 (CH, C7), 29.6 (CH2, C13), 31.7 (CH2, C10), 35.9 [CH, 9-CH(CH3)2], 36.1 (CH2, C6), 107.2 (C, d, J ? 11.5 Hz, C12a), 112.2 (CH, d, J = 23.3 Hz, C2), 115.7 (C, C11a), 116.3 (CH, C4), 122.2 (CH, C8), 134.9 (CH, d, J ? 11.5 Hz, C3), 140.6 (C, C4a), 144.5 (C, C9), 152.9 (C) and 155.3 (C) (C5a and C12), 161.1 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H21FN2·HCl·3/4H2O (346.36): C, 65.89; H, 6.84; N, 8.09; Cl, 10.24. Found: C, 65.55; H, 6.62; N, 7.99; Cl, 10.21.

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

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 77326-36-4, 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.

To a solution of 2-ethylbutan-l-ol (1.02 g, 10.0 mmol) in dry THF (60 mL) was carefully added NaH (60% in mineral oil, 480 mg, 12.0 mmol) in small portions at 0 C under nitrogen. The reaction mixture was stirred at 0 C under nitrogen for 2 hrs. To this solution was added 2- amino-6-fluorobenzonitrile (1.36 g, 10.0 mmol), and the reaction solution was stirred at 0 C – RT for 2 hrs, and then at 65 C overnight under nitrogen. The reaction was cooled down to room temperature then quenched with brine, and extracted with EtOAc (3X). The combined organic layers were washed with brine, dried over Na2S04. Filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: 20% EtOAc in hexanes) to give the title compound as colorless oil (1.29 g, 59%). 1H NMR (400 MHz, CDC13) delta 0.93 (t, J= 8 Hz, 6H), 1.55-1.43 (m, 4H), 1.73- 1.65 (m, 1H), 3.90 (d, J= 4 Hz, 2H), 4.10 (brs, 2H), 6.25 (d, J = 8 Hz, 1H), 6.34 (d, J = 8 Hz, 1H), 7.20 (t, J = 8 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Application 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.

Example 2;: N,N-Dimethyl-2-cyano-3-methoxyphenylsulfonamide (Compound No. 2); 2.1 : 2-Amino-6-methoxybenzonitrile; EPO A solution of 70 g (0.5 mol) of 2-amino-6-fluorobenzonitrile (prepared, e.g. according to US 4,504,660) in 250 ml of N,N-dimethylformamide was prepared, and a solution of 30.6 g (0.55 mol) of sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours with stirring. The completion of the reaction was monitored by TLC. An additional 25 g of sodium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for an additional 4 hours while stirring. The reaction mixture was concentrated under reduced pressure. The resulting residue was triturated with water, filtered off with suction and the solids obtained were dissolved in ethyl acetate. The resulting solution was concen- trated in vacuo. The obtained residue was triturated with petroleum ether and filtered off with suction. Yield: 48 g (63% of theory) of a brownish solid having a melting point of 143-146C.

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

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., Recommanded Product: 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+).

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 77326-36-4, Formula: C7H5FN2

NaOMe(25%wtinMeOH,325muL,1.42mmol,1.1eq.)wasaddedtoasolutionof2-amino-6-fluorobenzonitrile (176 mg, 1.29 mmol, 1.0 eq.) in DMF (1.00 mL) at roomtemperature, and stirred for 18 hours. The solution was concentrated in vacuo and theresidue stirred with H2O (10 mL) to give a beige precipitate. This was filtered underreducedpressure,theresiduedissolvedinEtOAcandconcentratedinvacuo,tituratedwithhexanes before remaining solvent was removed in vacuo giving 2-amino-6-methoxybenzonitrile(158mg,1.07mmol,83%)asabeigeamorphoussolid;mp143-145C,lit.136-140C.13

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Sutherell, Charlotte L.; Ley, Steven V.; Synthesis; vol. 49; 1; (2017); p. 135 – 144;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts