Category: nitriles-buliding-blocks

Reference of 3598-13-8, A common heterocyclic compound, 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, molecular formula is C8H6ClNO, 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.

A. (5-Amino-2-chloro-4-pyridyl) acetonitrile To a stirred solution of potassium t-butoxide (24.69 g, 220 mmol, 2.2 eq) in anhydrous tetrahydrofuran (150 ml) at -50C under nitrogen, a solution of 2-chloro-5-nitropyridine (15.85 g, 100 mmol) and (4-chlorophenoxy)acetonitrile (E. Grochowski et al., Bull. Acad. Pol. Sci. Ser. Sci. Chim ., 11 , 443 (1963)) (18.44 g, 110 mmol, 1.1 eq) in anhydrous tetrahydrofuran (150 ml) was added dropwise at such a rate that the reaction temperature was maintained at -40 to -50C with cooling in a dry ice/acetone bath. The resultant purple colored reaction mixture was then stirred at -78C under nitrogen for 1 hour, at which time glacial acetic acid (20 ml, 0.35 mol, 3.5 eq) was added to the reaction, and the mixture was allowed to warm to room temperature. A solution of 5% HCl (100 ml) was added to the reaction mixture and this aqueous mixture was extracted with ethyl ether (100 ml) and then with methylene chloride (2×100 ml). The extracts were combined, dried over magnesium sulfate, and passed through a silica gel filter (approximately 150 g) followed by methylene chloride (1200 ml). This filtrate was evaporated under reduced pressure, and the residual oil was chromatographed using silica gel (approximately 300 g) and eluted with 25% hexanes in methylene chloride to afford an oil (Rf=0.52 in methylene chloride) which was triturated in cold anhydrous ether to afford 6-chloro-3-nitro-2-pyridyl acetonitrile (1.37 g, 7%) as a white crystalline solid: mp, 121.5-123.5C.

The synthetic route of 3598-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; EP436333; (1991); A2;,
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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. 70591-86-5, name is 3-Bromobenzoylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H6BrNO

To a solution of 3-(3-bromophenyl)-3-oxopropanenitrile (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (×1). The organic layer was washed (water, brine), dried over Na2SO4and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification.

The synthetic route of 70591-86-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORP; COWAN, D. J; LARKIN, A. L.; ZHANG, CUNYU; MUSSO, D. L.; GREEN, G. M.; CADILLA, R.; SPEARING, P.K.; BISHOP, M. J.; SPEAKE, J. D.; (219 pag.)CN102516115; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, 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 52133-67-2, name: Ethyl 2-cyano-4,4-diethoxybutyrate

To a solution of nicotinimide amide (5.03 g, 41.6 mmol, 1.2 eq) in EtOH (100 mL)NaOMe (4.8 g, 88.8 mmol, 2.5 eq) was added.The mixture was stirred at room temperature for 4 hours.The reaction mixture was added to ethyl 2-cyano-4,4-diethoxybutanoate (8.00 g, 34.9 mmol, 1 eq). The mixture was stirred at 105 ° C. overnight.After cooling, the reaction mixture was acidified with cone. HCl and stirred at room temperature for 2 hours.A precipitate formed, which was collected and washed with H 2 O (20 mL × 2).Upon lyophilization, 3.10 g of the product was obtained as a grayish yellow solid (yield 41.8percent).

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Reference:
Patent; OTSUKA PHARMACEUTICAL COMPANY LIMITED; SUZUKI, MASAKI; KONDO, KAZUMI; KURIMURA, MUNEAKI; VALLURU, KRISHNA REDDY; TAKAHASHI, AKIRA; KURODA, TAKESHI; TAKAHASHI, HARUKA; FUKUSHIMA, TAE; MIYAMURA, SHIN; GHOSH, INDRANATH; DOGRA, ABHISHEK; HARRIMAN, GERALDINE; ELDER, AMY; SHIMIZU, SATOSHI; HODGETTS, KEVIN J; NEWCOM, JASON S; (678 pag.)JP6121658; (2017); B2;,
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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 5332-06-9 as follows. Product Details of 5332-06-9

To a stirred suspension of NaH (0.092g, 60% dispersion in mineral oil, 1.2 mmol) in THF (15 mL) at 0 C was added dropwise a solution of 4 (0.5 g, 1 mmol) in THF (15 mL). The mixture wasstirred 0 C for 10 min and then a solution of 4-bromobutyronitrile (0.34 g,0.228 mL, 1.2 mmol) in THF (5 mL) was added slowly. The mixture was allowed towarm to r.t. and stirred overnight. It was then cooled to 0 C and cold water(5 mL) was added very slowly and extracted with ethyl acetate (2 x 15 mL). Thecombined organic phase was washed with water (3 x 10 mL), brine (10 mL), driedover Na2SO4 and evaporated. The product 5 (0.56 g,92%) was obtained by column chromatography on silica gel using pet ether: ethylacetate as an eluents.

According to the analysis of related databases, 5332-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pakhare, Deepali S.; Kusurkar, Radhika S.; Tetrahedron Letters; vol. 56; 44; (2015); p. 6012 – 6015;,
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Adding a certain compound to certain chemical reactions, such as: 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, 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 42872-83-3, HPLC of Formula: C8H6BrN

Scheme VI begins with the bromination Reaction 1 of a 4-bromotoluene XXXII with N-bromosuccinamide (NBS) and benzoyl peroxide in chloroform.

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-Bromo-5-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ZECH, Stephan, G.; KOHLMANN, Anna; LI, Feng; WANG, Yihan; ZHOU, Tianjun; DALGARNO, David, C.; SHAKESPEARE, William, C.; ZHU, Xiaotian; WO2014/151761; (2014); A1;,
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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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 630-18-2

1-(Benzo[h]quinolin-2-yl)-2,2-dimethylpropanone. A solution of 2-bromobenzo[h]quinoline (1.52 g, 5.89 mmol) in THF (36 ml) was cooled to -78 C. and after 10 minutes a solution of 2.5 M of n-butyllithium in n-hexane (2.47 ml, 6.18 mmol) was added slowly. The resulting dark red solution was stirred at this temperature for 1 hour and then a solution of 2,2-dimethylpropanonitrile (0.78 ml, 7.04 mmol) in THF (5 ml) was added drop-wise. The solution was stirred for a further hour at -78 C. and finally allowed to warm slowly to ambient temperature. A solution of 1M H2SO4 (25 ml, 25 mmol) was then added and the mixture was heated under reflux for 3 hours. After cooling, the organic phase was separated and the aqueous phase was extracted with Et2O (3*15 ml). The organic phases were combined, dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (eluent: petroleum ether/acetate=9/1) to give 1.24 g (80% yield) of 1-(benzo[h]quinolin-2-yl)-2,2-dimethylpropanone in the form of a yellow solid; melting point: 88-90 C. Elemental analysis (%) calculated for C18H17NO: C, 82.10; H, 6.51; N, 5.32. Found: C, 82.10; H, 6.51; N, 5.32. 1H NMR (CDCl3): delta 9.20 (d, J=7.8 Hz, 1H), 8.13 (s, 2H), 7.84 (d, J=7.8 Hz, 1H), 7.80-7.73 (m, 2H), 7.73-7.62 (m, 1H), 7.56 (d, J=9 Hz, 1H), 1.67 (s, 9H). 13C{1H} NMR (CDCl3): delta 206.7, 152.1, 144.5, 136.3, 133.7, 131.8, 129.5, 128.4, 127.9, 127.5, 124.9, 124.5, 121.2, 44.3, 28.0.

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:
Patent; Rigo, Pierluigi; Baratta, Walter; Siega, Katia; Chelucci, Giorgio Adolfo; Ballico, Maurizio; Magnolia, Santo; US2010/152448; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 57381-51-8, name is 4-Chloro-2-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 57381-51-8, Recommanded Product: 57381-51-8

[00088] To a stirred solution of 4-chloro-2-fluorobenzonitrile 15 (1 g, 6.41 mmol) in DMF (25mL) under inert atmosphere was added cesium carbonate (2.30 g, 7.05 mmol) at RT; heated to40 C and to this was added (4-methoxyphenyl) methanethiol 8 (1.08 g, 7.05 mmol); heated to 60C and stirred for 2 h. The reaction was monitored by TLC; after completion of the reaction, thereaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 25 mL). Thecombined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo toobtain the crude. The crude was purified through silica gel column chromatography using 4%EtOAc/ hexanes to afford compound 16 (900 mg, 48%) as white solid. TLC: 10% EtOAc/hexanes (R 0.6); 1H-NMR (CDC13, 400 MHz): oe 7.51 (d, J 8.4 Hz, 1H), 7.33 (s, 1H), 7.23-7.20 (m, 3H), 6.84 (d, J= 8.4 Hz, 2H), 4.19 (s, 2H), 3.79 (s, 3H).

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Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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 175596-01-7, Product Details of 175596-01-7

EXAMPLE 20B methyl 2-fluoro-4-formylbenzoate EXAMPLE 20A (310 mg, 1.73 mmol) was dissolved in 60% aqueous acetic acid (10 mL) with warming. Raney nickel (60 mg) was added and the mixture was stirred under hydrogen at ambient temperature for 18 hours. Solid material was filtered off and the filtrate concentrated. The residue was purified on silica gel using 1:4 ethyl acetate/hexane to give the title compound (220 mg, 70%). MS (DCI): m/z 183 (M+H)+.

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Reference:
Patent; Penning, Thomas D.; Thomas, Sheela A.; Zhu, Gui-Dong; Gong, Jianchun; Giranda, Vincent L.; Gandhi, Viraj B.; US2007/112047; (2007); A1;,
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Synthetic Route of 874-90-8, These common heterocyclic compound, 874-90-8, name is 4-Methoxybenzonitrile, 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.

Bis(4-methoxyphenyl)methammine (1) was prepared according to the procedure described in Pickert et al., (1973) Organic Syntheses Coll. Fpp520-522 and Dejaegher et al., (2002) Synlett 113-115. Magnesium (0.76 g) was suspended in 30 mL dry THF in a flame-dried 3-neck round-bottomed flask equipped with a stir bar. Some drops of 4-bromoanisole were added, and to initiate the reaction, a crystal of iodine was added and the solution heated to a gentle reflux (-6O0C). Once the color of the iodine had disappeared, the remaining l-bromo-4- methoxybenzene (3.9 mL) in 8 mL THF was added. The mixture was refluxed for 45 minutes. After cooling to RT, 2.5 g of p-methoxybenzonitrile in dry THF was added over 20 minutes and reacted for 6 h under reflux. The reaction mixture was cooled and 4.5 mL of methanol added to quench the reaction. After stirring for 20 minutes, it was concentrated to remove THF, redissolved in CH2Cl2 and quickly washed with water in a separatory funnel to remove Mg salts. The CH2Cl2 layer was dried over MgSO4, concentrated, redissolved in a minimal amount of dichloromethane and diethyl ether added to precipitate white shiny crystals of Bis(4- methoxyphenyl)methanimine (4.01 g, 59% yield). It is worthy of mention that the preparation of this diarylketimine was simple and efficient resulting in crystals without any additional lengthy purification steps such as distillation or chromatography which contributes to the simpler glycosylation chemistry. Rf = 0.32 (60% EtOAc: hexanes), m.p. = 128-129 0C, 1H NMR (CDCl3, 500 MHz) d 3.84 (6H, s), 6.90 (4H, d, J= 9.0 Hz), 7.52 (4H, d, J= 8.5 Hz), 8.95 (NH, broad) ; 13C NMR (CDCl3, 500 MHz) d 55.3 (2CH3O), 113.4 (4CH), 129.98 (4CH), 132.1(2C, q), 161.1 (2C- O, q), and 176.9 (C=N).

Statistics shows that 4-Methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 874-90-8.

Reference:
Patent; THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA; WO2007/55698; (2007); A1;,
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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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H9N

Preparation of the imino ester: A mixture of 8.3 g (0.1 mole) of trimethyl acetonitrile and 5.05 g of EtOH (0.11 mole) is treated with HCI gas at 5 0C until saturation. The mixture is then stored at the same temperature for 18 h and 20 ml of DEE are added. The resulting precipitate is collected by filtration, ished with DEE and dried to yield 3.9 g (24%) of the crude imino ester hydrochloride as a white solid. (1H- NMR (400 MHz, DMSO-O6): delta = 4.42 (q, 2H), 1.35 (t, 3H), 1.25 (s, 9H)).

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:
Patent; NOVARTIS AG; WO2008/71404; (2008); A1;,
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