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

HRID 848477
Notes
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Reaction equation

HRID 848477 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 205654663-Chloro-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one

Product 1

HCID 205654901-(4-Chlorophenyl)-3-cyano-1,2-dihydroquinoxalin-2-oneYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. extractionthe product was extracted into chloroform
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes