Hydrochloric Acid → HCID 54504810, compound

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Reaction Conditions

Reaction Steps

138 g (1 mole) of m-nitro-aniline are slowly added in a 2-liter reactor to a mixture of 300 ml of concentrated HCl, 150 ml of water and 150 ml of acetic acid. The mixture is heated until the amine hydrochloride dissolves, whereafter the mixture is cooled to 0° C. with vigorous agitation. With the temperature remaining between 0° and 3° C., 70 g of NaHO2 dissolved in 150 ml of H2O are added.. The m-nitro-benzene-diazonium chloride solution is added simultaneously with an aqueous solution of 25 g of CuCl2.2H2O to a solution of 87 g of α-chloro-acrylonitrile in 150 ml of acetone. The temperature is kept at 30° C. Evolution of nitrogen ceases after about 6 hours. The α,α-dichloro-β-(3-nitrophenyl)propionitrile is extracted with benzene, washed in sodium hydroxide, then washed with water. After drying and removal of the solvent the product is distilled at low pressure. 215 g of α,α-dichloro-β-(3-nitrophenyl)propionitrile, corresponding to an 88% yield, are obtained, in the form of a slightly pinkish oil distilling at 140° C. at a pressure of 0.1 mm.

Provenance & Evidence