Category: 60899-34-5

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. 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H7NO

a 4-Thiocarbamoyl-2,3-dihydro-1H-inden-1-one A solution of 12.1 g (77 mmol) of 4-cyano-2,3-dihydro-1H-inden-1-one ?see Coll. Czechoslov. Chem. Commun. 4, 3227[(1978)] in 220 ml of pyridine and 10.6 ml (77 mmol) of triethylamine is saturated with hydrogen sulfide for 3 hours at 40 and is then stirred at the same temperature for 16 hours. The reaction mixture is cooled and then concentrated to dryness by evaporation, and 300 ml of water are added to the residue. The yellow product that has crystallized out is filtered off with suction, washed with water, dried and recrystallized from ethyl acetate. In that manner there is obtained the title compound, m.p. 197 (decomp.).

The synthetic route of 60899-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US5840911; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 60899-34-5, 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. 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

stirred suspension of l-oxo-2,3-dihydro-iH-indene-4-carbonitrile (1.2 g, 7.64 mmol) and silica gel (catalytic) in EtOH at 0C was added NaBH4 (237.2 mg, 7.64 mmol). The reaction was allowed to warm to room temperature and stirred for 2 h. The solvent was removed under reduced pressure, and the product was purified by chromatography (50% EA/hexane) to afford 1.02 g (82.3%) of l-hydroxy-2,3-dihydro- iH-indene-4-carbonitrile as white solid. LCMS-ESI (m/z) calculated for C10H9NO; 159.18; found 160.1 [M+H]+, tR = 2.39 min.

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, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RECEPTOS, INC.; MARTINBOROUGH, Esther; BOEHM, Marcus, F.; YEAGER, Adam, Richard; TAMIYA, Junko; HUANG, Liming; BRAHMACHARY, Enugurthi; MOORJANI, Manisha; TIMONY, Gregg, Alan; BROOKS, Jennifer, L.; PEACH, Robert; SCOTT, Fiona, Lorraine; HANSON, Michael, Allen; WO2015/66515; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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.

A stirred mixture of 1 -oxo-2,3 -dihydro- 1 H-indene-4-carbonitrile (mt 1) (20.Og, 98 wt%, 18.6 assay g, 124.8 mmol) in abs EtOH (20 mL), triethylorthoformate (80 mL, 481 mmol) and methanesulfonic acid (0.88 mL, 12.5 mmol) in toluene (80 mL)was heated at 43 -47C. After 1 h, GC analysis showed orthoformate consumed and 12.8 area% of mt 1 remaining. A further charge of triethylorthoformate (20 mL, 120.2 mmol) was made and after 45 mm GC analysis showed 1.5 area% mt 1. The batch was cooled to ambient temperature and then poured into 1 M aq. K2HPO4 (200 mL) with vigorous stirring while maintaining a quench temperature < 15 C. The two-phasemixture was vigorously stirred for 10 mm. The phases were separated and the aqueous phase (pH 11) was back extracted with toluene (100 mL). The organic phases were combined and distilled at atmospheric pressure to remove 340 mL distillate. Toluene was added (500 mL) and distilled at atmospheric pressure to remove 500 mL distillate. Total distillation time 3 h, temperature range 80-120 C. At this point the batch wasstored overnight at < 5 C. Excess orthoformate was removed by chasing with ethyl acetate (100 mL) under reduced pressure until distillation stopped. Another volume of ethyl acetate (100 mL) was added and then concentrated under reduced pressure until distillation stopped. A third volume of ethyl acetate (100 mL) was added and then concentrated under reduced pressure until distillation stopped, after which GC analysisconfirmed no orthoformate remaining. The crude was then stirred at 110 C for 1 h, to convert the intermediate ketal to 3-ethoxy-1H-indene-7-carbonitrile (mt 2). Upon cooling, the crude (mobile oil, 21.34 g) was assayed for mt 2 by ?H NIVIR employing mesitylene as an internal standard. The oil assayed at 78.1 wt% product = 16.73 assay g, 90.0 mmol = 72.1 % assay yield. The crude oil was then purified by filtration througha silica gel plug eluting with 15% EtOAc/hexane. The pure fractions were combined and utilized for the next step. ?H NIVIR (400 MHz, d6-DMSO) 7.78 (d, J = 8.4, 1H), 7.63 (m, 1H), 7.49 (m, 1H), 5.60 (m, 1H), 1.38 (t, J= 6.8 Hz, 1H), 1.19 (t, J= 6.8 Hz, 1H); LRMS: calcd for C,2H,2NO [M + H]: 186.2; Found: 186.2. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common. Reference:
Patent; CELGENE INTERNATIONAL II SARL; MEADOWS, Kristen, R., Taylor; SKOLNICK, Brett; DALVIE, Deepak; (78 pag.)WO2018/208855; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 60899-34-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 60899-34-5 as follows.

In a 25 mL single-necked flask, 2,3-dihydro-1-oxo-1H-indene-4-carbonitrile (1.57 g), tetraisopropyl titanate (2.74 g), and S-phenylethylamine (1.45 g), toluene (15 mL), and stirred with heating to 100 C; After the reaction was completed, the temperature of the system was lowered to below 35 C, and an aqueous solution (20 mL) of sodium hydroxide (0.48 g) was added, and the filtrate was collected by stirring and filtration. The filtrate was concentrated to obtain 2.3 g of (S,Z)-1-((1-phenylethyl)imino)-2,3-dihydro-1H-indene-4-carbonitrile with a yield of 87.8% and a purity of 95.0%.

According to the analysis of related databases, 60899-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Xu Guobin; Sun Guodong; Wang Zhongqing; Hu Yanqing; Su Wei; Luo Zhonghua; Huang Fangfang; (9 pag.)CN110615747; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 the stirred mixture of 50.0 gm of 4-cyano-l-indanone (Formula 3) (0.318 moles) and 500 ml of heptane, 60 gm of (S)-(-)-l-(4-methoxyphenyl)ethylamine (Formulal3) (0.398 moles, 1.25eq.) was added at ambient temperature. The resulting mixture was heated to 100-105C and water was removed azeotropically. After 15.0 hrs, the reaction mass was cooled to 25-30C and stirred for 1.0 hr. The product was filtered, washed with heptane and dried to obtain a light brown solid of compound of Formulal4(84.0 g, 90.93% yield) with HPLC purity 94.35% & SOR -72 (c=0.1 in CHC13at 20C).MR: 130.4-132.1C; IR (KBr, cm”1): 2226, 1661, 1611, 1513, 1245, 1030; 1H- NMR(CDC13): delta 8.11-8.09 (d, 1H, J=7.74Hz), 7.66-7.64 (d, 1H, J=7.47Hz),7.41-7.89 (m, 3H), 6.89-6.87 (d, 2H, J=8.50Hz), 4.66-4.61 (q, 1H, J=6.46, 12.96 Hz), 3.79 (s, 3H), 3.26-3.21 (m, 2H), 2.90-2.88 (m, 1H), 2.78-2.73 (m, 1H), 1.56-1.55 (d, 3H, J=6.49Hz);13C-NMR(CDCl3): 169.99, 158.48, 152.56, 141.66, 137.59, 134.28, 127.72, 127.66 (2C),127.15,117.12, 113.87(2C), 109.93, 61.56, 55.32, 27.85, 27.67, 24.77;MS (m/z): 291.1 [M+l]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; CHINNAPILLAI, Rajendiran; PERIYANDI, Nagarajan; JASTI, Venkateswaralu; (33 pag.)WO2019/58290; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 60899-34-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To 1-oxo-2,3-dihydro-JH-indene-4-carbonitrile INT-1 (42.5 g, 0.27 mol) and (R)-2-methylpropane-2-sulfinamide (36.0 g, 0.30 mol) in toluene (530 mL)was added titanium tetraethoxide (84.1 mL, 92.5 g, 0.40 mol) and the reaction mixture was heated at 60C for 12 h under N2. The crude (R)-N-(4-cyano-2,3-dihydro-1H- indene-1-ylidene)-2-methylpropane-2-sulfinamide INT-4 was used directly in the next experiment. LCMS-ESI (m/z) calculated for C14H16N20S: 260.3; found 261.1 [M+H],3.19 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; SCOTT, Fiona, Lorraine; MEADOWS, Kristen, R., Taylor; PEACH, Robert; (154 pag.)WO2018/64356; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H7NO

a 4-Thiocarbamoyl-2,3-dihydro-1H-inden-1-one A solution of 12.1 g (77 mmol) of 4-cyano-2,3-dihydro-1H-inden-1-one ?see Coll. Czechoslov. Chem. Commun. 4, 3227[(1978)] in 220 ml of pyridine and 10.6 ml (77 mmol) of triethylamine is saturated with hydrogen sulfide for 3 hours at 40 and is then stirred at the same temperature for 16 hours. The reaction mixture is cooled and then concentrated to dryness by evaporation, and 300 ml of water are added to the residue. The yellow product that has crystallized out is filtered off with suction, washed with water, dried and recrystallized from ethyl acetate. In that manner there is obtained the title compound, m.p. 197 (decomp.).

The synthetic route of 60899-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US5840911; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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. Application In Synthesis of 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile

To l-oxo-2,3-dihydro-7H-indene-4-carbonitrile INT-1 (42.5 g, 0.27 mol) and (i?)-2-methylpropane-2-sulfinamide (36.0 g, 0.30 mol) in toluene (530 mL) was added titanium tetraethoxide (84.1 mL, 92.5 g, 0.40 mol) and the reaction mixture was heated at 60C for 12 h under N2. The crude (i?)-N-(4-cyano-2,3-dihydro-lH- indene-l-ylidene)-2-methylpropane-2-sulfinamide INT-4 was used directly in the next experiment. LCMS-ESI (m/z) calculated for Ci4Hi6N2OS: 260.3; found 261.1 [M+H]+, = 3.19 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60899-34-5, its application will become more common.

Synthetic Route of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 3 -neck flask with an internal thermometer and an addition funnel was added (i?)-(+)-2-methyl-CBS-oxazaborolidine solution in toluene (3.0 mL) and borane-dimethylsulfide (300 The reaction was stirred at room temperature for 10 min then diluted with DCM (25 mL). Borane-dimethylsulfide (6.0 mL) was added and, after stirring for 5 min, the reaction was cooled to -20C. l-Oxo-2,3-dihydro-7H- indene-4-carbonitrile INT-1 (4.7 g, 30 mmol) in DCM (25 mL) was added dropwise by addition funnel over 20 min while maintaining the reaction at -20 ¡À 5C. The reaction was stirred for 1 h then quenched by the dropwise addition of MeOH (20 mL). After hydrogen evolution ceased, MeOH (30 mL) was added and removed by heating at atmospheric pressure. MeOH (50 mL) was added in two and removed by heating twice. All the solvent was evaporated to give a solid which was recrystallized from EA (9 mL) and hexane (22 mL). The compound was filtered and washed with 5: 1 hexane/EA (30 mL) to provide 3.73 g (78%) of (5)-l-hydroxy-2,3-dihydro-iH-indene-4-carbonitrile INT-2 as a white powder. LCMS-ESI (m/z) calculated for Ci0H9NO: 159.1; found 160.1 [M+H]+, tR = 2.39 min. 1H NMR (400 MHz, CDC13) delta 7.62 (d, J = 7.6 Hz, 1H), 7.53 (d, J = 7.6 Hz, 1H), 7.32 (t, J = 7.6 Hz, 1H), 5.28 (d, J = 4.1 Hz, 1H), 3.23 (ddd, J = 17.0, 8.7, 4.4 Hz, 1H), 3.04 – 2.90 (m, 1H), 2.64 – 2.51 (m, 1H), 2.00 (dddd, J= 13.4, 8.7, 7.1, 5.7 Hz, 1H), 1.91 (d, J = 5.4 Hz, 1H). Chiral HPLC: (5)-l-hydroxy-2,3- dihydro-iH-indene-4-carbonitrile was eluted in 20% IPA in hexane: >99.9% ee, = 7.42 min. The (i?)-enantiomer was obtained in an analogous fashion using (S) -(-)-2- methyl-CBS-oxazaborolidine. for (i?)-enantiomer = 6.79 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; RECEPTOS, INC.; MARTINBOROUGH, Esther; BOEHM, Marcus, F.; YEAGER, Adam, Richard; TAMIYA, Junko; HUANG, Liming; BRAHMACHARY, Enugurthi; MOORJANI, Manisha; TIMONY, Gregg, Alan; BROOKS, Jennifer, L.; PEACH, Robert; SCOTT, Fiona, Lorraine; HANSON, Michael, Allen; WO2015/66515; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 60899-34-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l-ylidene]-2-methylpropane-2- sulfinamide: To a solution of l-oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in Toluene (60 mL) was added (S)-2-methylpropane-2-sulfinamide (4.24 g, 34.98 mmol, 1.10 equiv), Ti(OEt)4 (10.75 g, 47.15 mmol, 1.48 equiv). The resulting solution was stirred for 16 h at 60 C. The resulting solution was used directly in the next step without further purification. LC-MS: m/z = 261 [M+H]+. To a solution of l -oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in toluene (50 mL) was added (S)-2-methylpropane-2-sulfinamide (4.6 g, 37.95 mmol, 1.20 equiv), Ti(OEt)4 (1 1 g, 1.50 equiv). The resulting solution was stirred for 18 h at 60 C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of sat. potassium sodium tartrate (30 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined, washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 5.5 g (66%) of (S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l -ylidene]-2- methylpropane-2-sulfinamide as a yellow green solid. LC-MS: m/z = 261 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts