4-Methoxy-o-phenylenediamine → HCID 491324, compound

HRID 1507417Notes

Reaction equation

HRID 1507417 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.[F:11][C:12]([F:21])([F:20])[C:13](=O)[C:14]([O:16]CC)=[O:15]>CCO.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:9][C:14](=[O:15])[C:13]([C:12]([F:21])([F:20])[F:11])=[N:10]2.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([N:9]=[C:13]([C:12]([F:11])([F:20])[F:21])[C:14](=[O:16])[NH:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 1534044-Methoxy-o-phenylenediamineHCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoate

Product 2

HCID 491324HCID 491324, compoundYield 42%HCID 11806856HCID 11806856, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxybenzene-1,2-diamine (2.00 g, 14.5 mmol) and ethyl trifluoropyruvate (2.47 g, 14.5 mmol) in absolute EtOH (30 mL) was refluxed overnight. The mixture was cooled to room temperature and diluted with EtOAc (300 mL), washed with water (100 mL x 2), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 6-methoxy-3-(trifluoromethyl)quinoxalin-2(1H)-one (1.50 g, yield 42%) as solid (also obtained 7-methoxy-3-(trifluoromethyl)quinoxalin-2(1H)-one (600 mg, yield 17%)).

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with water (100 mL x 2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6dbd785b976e48d898bf707731445c73
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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