Water → 1-(4-Chlorophenyl)-3-cyano-1,2-dihydroquinoxalin-2-one

HRID 848477Notes

Reaction equation

Cl[C:2]1[C:3](=[O:19])[N:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C-:20]#[N:21].[K+].O>CN(C)C=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:11]=[C:2]([C:20]#[N:21])[C:3]2=[O:19])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 3-chloro-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one (10.0 g) and potassium cyanide (2.5 g) in dry dimethylformamide (100 ml) was heated at 140° C. for 24 hours. The mixture was added to water and the product was extracted into chloroform. Evaporation of the solvent and crystallisation of the residue from ethanol gave the title compound (6.3 g) mp 232°-235° C.

Workup

extractionthe product was extracted into chloroform
customEvaporation of the solvent and crystallisation of the residue from ethanol

Sources & evidence

ORD record: ord-943ac14bea574d5d86eabdb074bc7e10
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04296114

Reaction notes

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