Synthesis of 2-chloro-3-(4-nitrophenyl)propanenitrile

Preparation of 2-chloro-3-(4-nitrophenyl)propanenitrile

Alternative Names: 2-chloro-3-(4-nitrophenyl)propanenitrile; BRN 1963899; 2-Chloro-3-(4-nitro-phenyl)-propionitrile; Alpha-Chloro-p-nitrohydrocinnamonitrile; 17849-31-9; Hydrocinnamonitrile, alpha-chloro-p-nitro-;

Preparation of 2-chloro-3-(4-nitrophenyl)propanenitrile

Preparation of 2-chloro-3-(4-nitrophenyl)propanenitrile

4.2 kg of p-nitroaniline are dissolved in a hot mixture of 9 l of concentrated hydrochloric acid and 9 l of water, cooled to 30° C, and treated with 24 kg of ice. 7.3 l of 30% sodium nitrite solution are added in within a few minutes with vigorous cooling. The diazonium salt solution is filtered and treated with a solution of 1.76 kg of acrylonitrile in 15 l of acetone. 600 g of copper(II) chloride are then added and a short time thereafter at ca. 18° C evolution of nitrogen begins. The temperature is kept below 30° C by ice-cooling. 2-chloro-3-(4-nitrophenyl)propanenitrile separates and after recrystallization from methanol has m.p. 110° C. The yield of 2-chloro-3-(4-nitrophenyl)propanenitrile  is 5.3 kg.

Angew. Chem., 61, 179 (1949).

IUPAC Name

2-chloro-3-(4-nitrophenyl)propanenitrile

InChI

InChI=1S/C9H7ClN2O2/c10-8(6-11)5-7-1-3-9(4-2-7)12(13)14/h1-4,8H,5H2

InChI Key

MZPNWHGZPIHRNC-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1CC(C#N)Cl)[N+](=O)[O-]

Depositor-Supplied Synonyms

2-chloro-3-(4-nitrophenyl)propanenitrile, BRN 1963899, 2-Chloro-3-(4-nitro-phenyl)-propionitrile, alpha-Chloro-p-nitrohydrocinnamonitrile, 17849-31-9, Hydrocinnamonitrile, alpha-chloro-p-nitro-, AC1Q1XNF, AC1L220T, SCHEMBL3126907, CTK4D6802, MolPort-000-454-056, BB_SC-0413, BBL013009, STK803581, AKOS001074355, AKOS016244935, MCULE-8315939226, NE45377, Benzenepropanenitrile, a-chloro-4-nitro-, LS-77224, OR097676, 2-Chloro-3-(4-nitro-phenyl)-propanenitrile, EU-0002058, ST50076872, EN300-04323, 4-09-00-01776 (Beilstein Handbook Reference), T0511-4699

Removed Synonyms

CID64831

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