2,3-Diaminobenzoic acid → 3-(3-(Trifluoromethoxy)phenyl)quinoxaline-5-carboxylic acid

HRID 2359419Notes

Reaction equation

HRID 2359419 reaction equation
O=[C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:15])([F:14])[F:13])[CH:6]=1)[CH:3]=O.[NH2:16][C:17]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20]>CCO>[F:13][C:12]([F:15])([F:14])[O:11][C:7]1[CH:6]=[C:5]([C:2]2[CH:3]=[N:26][C:25]3[CH:24]=[CH:23][CH:22]=[C:18]([C:19]([OH:21])=[O:20])[C:17]=3[N:16]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1980692,3-Diaminobenzoic acidHCID 22273598(3-Trifluoromethoxyphenyl)oxoacetaldehyde

Product 1

HCID 581545253-(3-(Trifluoromethoxy)phenyl)quinoxaline-5-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-oxo-2-(3-(trifluoromethoxy)phenyl)acetaldehyde (1.0 g, 4.58 mmol) and 2,3-diaminobenzoic acid (634 mg, 4.17 mmol) were dissolved in EtOH (70 mL), and stirred at room temperature overnight. The volume was reduced to 30 mL, the precipitate was collected by filtration, washed with ethanol, and dried under vacuum to give 3-(3-(trifluoromethoxy)phenyl)quinoxaline-5-carboxylic acid as a gray solid (1.0 g, yield: 72% yield).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with ethanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b33a26758f6d416a9ee33c8c36ba3fbb
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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