4-Chlorophenylglyoxylic acid → 3-(4-chlorophenyl)-1-(2,2-difluoroethyl) quinoxalin-2(1H)-one

HRID 76361

Reaction equation

HRID 76361 reaction equation
[F:1][CH:2]([F:12])[CH2:3][NH:4][C:5]1[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[C:21](O)=[O:22])=[CH:16][CH:15]=1>CO>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:22])[N:4]([CH2:3][CH:2]([F:12])[F:1])[C:5]3[C:6]([N:11]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 1459984-Chlorophenylglyoxylic acidHCID 58110951N-(2,2-difiuoroethyl)benzene-1,2-diamine

Product 1

HCID 442244853-(4-chlorophenyl)-1-(2,2-difluoroethyl) quinoxalin-2(1H)-oneYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 400 mg (2.32 mM) of N-(2,2-difiuoroethyl)benzene-1,2-diamine in 7 ml of methanol were added 428 mg (2.32 mM) of 4-chloro-α-oxo-benzeneacetic acid. The mixture was refluxed for 3 h. A solid was filtered, washed and dried under vacuum to give 236 mg of 3-(4-chlorophenyl)-1-(2,2-difluoroethyl) quinoxalin-2(1H)-one Yield: 32%.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationA solid was filtered
  3. washwashed
  4. customdried under vacuum

Sources & evidence

ORD record
ord-64dbb87d1d4448acb783fc0babcb10cf
Source dataset
uspto-grants-2014_09
Patent number
US08835634B2

Linked notes

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