Water → 1-Benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acid

HRID 2269733Notes

Reaction equation

HRID 2269733 reaction equation
O.[OH-].[Na+].[CH2:4]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([C:21]([O:23]CC)=[O:22])[C:12]1=[O:26])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[CH2:4]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([C:21]([OH:23])=[O:22])[C:12]1=[O:26])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15461773HCID 15461773, compound

Product 1

HCID 154617741-Benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (15 ml) and sodium hydroxide (1.3 g) were added to a methanol (30 ml) solution of ethyl 4-benzyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxylate (3.5 g). The reaction mixture was stirred at room temperature for 2 hours and concentrated. 2N Hydrochloric acid was added to the residue to adjust the pH to 4, which was extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain the entitled compound (2.9 g).

Workup

  1. concentrationconcentrated
  2. addition2N Hydrochloric acid was added to the residue
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2f54472b0b9042f892843907632592cf
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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