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3-Chloro-4-nitro-benzonitrile Sodium nitrite (6.78 g in water (40 mL) at 0 C.) was slowly added to a solution of 4-amino-3-chloro-benzonitrile (10.5 g) in water (30 mL) and concentrated hydrochloric acid (30 mL) also at 0 C. After 10 minutes the solution was poured onto a suspension of cuprous oxide (3.48 g) and sodium nitrite (31.69 g) in water (100 mL) at 0 C. The ensuing mixture was stirred at 0 C. for 1 hour then at 23 C. for 1 hour. The resulting mixture was extracted with dichloromethane and the organic layer washed with saturated sodium chloride. The separated organic layer was dried over sodium sulfate and then concentrated to give 3-chloro-4-nitro-benzonitrile (11.31 g).
With urea; sodium nitrite; In sulfuric acid; water; ethyl acetate;
D. Ethyl 4-hydroxy-3-methylbenzoate Ethyl 4-amino-3-methylbenzoate (3.85 g; 21.5 mmol) was dissolved in hot, 35% H2 SO4 /water and the mixture then cooled to below 5 C. An ice-cold solution of 1.91 g (22.5 mmol) of sodium nitrite in 20 ml of water was then slowly added to the mixture such that the temperature of the mixture never exceeded 5 C. The mixture was stirred at 5 C. for 10 minutes and then treated with 1 g of urea and stirred for a further 10 minutes. A solution of 50 g (207 mmol) of cupric nitrate trihydrate in 750 ml of water was added to the reaction mixture followed by 2.87 g of cuprous oxide. The mixture was stirred for a further 15 minutes and then extracted with 3*300 ml ether. The ether extracts were combined and then washed with water and saturated NaCl solution and then dried (MgSO4). The solution was filtered, the solvent removed in-vacuo and the residue purified by flash chromatography (silica; 13% ethyl acetate in hexanes to 20% ethyl acetate in hexanes) to give the title compound as a pale yellow solid. PMR (CDCl3): delta 1.39 (3H, t, J~7.1 Hz), 2.28 (3H, s), 4.37 (2H, q, J~7.1 Hz), 6.87 (1H, d, J~8.5 Hz), 7.38 (1H, s), 7.79 (1H, dd, J~8.5 Hz, 2.0 Hz), 7.85 (1H, d, J~2.0 Hz).
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