N-cyclopropyl-N-(2-nitro-phenyl)-oxalamic acid methyl ester → 1-Cyclopropyl-4-hydroxy-1,4-dihydro-quinoxaline-2,3-dione

HRID 1966978Notes

Reaction equation

HRID 1966978 reaction equation
C[O:2][C:3](=O)[C:4]([N:6]([CH:16]1[CH2:18][CH2:17]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=[O:14])=[O:5]>CO.[Pd].C(OCC)(=O)C>[CH:16]1([N:6]2[C:7]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:13]([OH:14])[C:3](=[O:2])[C:4]2=[O:5])[CH2:18][CH2:17]1

Participants

5

Reactant 1

HCID 67320928N-cyclopropyl-N-(2-nitro-phenyl)-oxalamic acid methyl ester

Product 1

HCID 673201301-Cyclopropyl-4-hydroxy-1,4-dihydro-quinoxaline-2,3-dioneYield 84.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-cyclopropyl-N-(2-nitro-phenyl)-oxalamic acid methyl ester (45.0 g, 0.17 mol, 1.0 equiv) in methanol (400 mL) was added palladium on carbon (4.52 g, 0.0043 mol, 0.025 equiv; 10% Pd/C; [CAS RN 7440-05-3]) and the reaction mixture stirred under an atmosphere of hydrogen (1.2 bar) at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate (400 mL), filtered over Celite® and the solvent mixture removed by evaporation under reduced pressure to give 31.2 g (84%) of the title compound as a light yellow solid. MS (ISN): m/z=219.1 [M+H]+.

Workup

  1. filtrationfiltered over Celite®
  2. customthe solvent mixture removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b03342d0a77f44f9bbf9b26549786774
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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