Methyl 2-[(2-nitrophenyl)amino]acetate → 2(1H)-Quinoxalinone, 3,4-dihydro-

HRID 901940

Reaction equation

HRID 901940 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O>C(OCC)(=O)C.CO.[Pd]>[NH:12]1[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][CH2:4][C:3]1=[O:2]

Participants

5

Reactant 1

HCID 11252796Methyl 2-[(2-nitrophenyl)amino]acetate

Product 1

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-Yield 99.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(2-nitrophenyl)glycine methyl ester (740 mg, 3.6 mmol) in ethyl acetate (50 ml) and methanol (25 ml) was hydrogenated at atmospheric pressure over a catalytic amount of 10% palladium on carbon. After 1 h the mixture was filtered and reduced to afford 1,2,3,4-tetrahydroquinoxalin-2-one as a yellow solid (530 mg, 99%).

Workup

  1. filtrationAfter 1 h the mixture was filtered

Sources & evidence

ORD record
ord-b71da26728394ec1875e6794cb8bd16c
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Linked notes

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