Phenylglyoxylic Acid → 1-(4-Chlorophenyl)-3-phenylquinoxalin-2(1H)-one

HRID 848472Notes

Reaction equation

HRID 848472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[C:16]([C:24](O)=[O:25])(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:24]2=[O:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11915Phenylglyoxylic AcidHCID 522323N-(4-chlorophenyl)benzene-1,2-diamine

Product 1

HCID 133813051-(4-Chlorophenyl)-3-phenylquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-(4-chlorophenyl)benzene-1,2-diamine (12.0 g) in a minimum quantity of ether was added benzoylformic acid (7.5 g) dissolved in ether and the mixture was stirred for 8 hours. The resulting precipitate was filtered, dried, and recrystallised from ethanol giving the title compound (11.0 g) mp 214.5°-216.5° C.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried
  3. customrecrystallised from ethanol giving the title compound (11.0 g) mp 214.5°-216.5° C.

Sources & evidence

ORD record
ord-b0d02b3b78e2433f8ecf759c0b52b500
Source dataset
uspto-grants-1981_10
Patent number
US04296114

Reaction notes

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