Methyl 2-acetylamino-4-nitrobenzoate → Methyl 2-acetylamino-4-aminobenzoate

HRID 354512Notes

Reaction equation

HRID 354512 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH:4][C:5]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 12399497Methyl 2-acetylamino-4-nitrobenzoate

Product 1

HCID 12399498Methyl 2-acetylamino-4-aminobenzoateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-acetylamino-4-nitrobenzoate (1.31 g, 5.50 mmol) in MeOH (30 mL) was added 5% Pd on carbon (195 mg), and the stirring under H2 gas (3 atm) was continued for 18 hours at rt. The catalyst was filtered off and the mixture was evaporated. The resulting crude solid was recrystallized with CHCl3—MeOH-hexane to give methyl 2-acetylamino-4-aminobenzoate (1.03 g, 90%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ2.23 (s, 3 H), 3.82 (s, 3 H), 4.20 (s, 2 H), 6.30 (dd, J=2.5 Hz, 8.8 Hz, 1 H), 7.80 (d, J=8.8 Hz, 1 H), 8.06 (s, 1 H), 11.26 (s, 1 H); MS (FAB), m/z 208 (M+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe mixture was evaporated
  3. customThe resulting crude solid was recrystallized with CHCl3—MeOH-hexane

Sources & evidence

ORD record
ord-f834d295e3de4c14ae89f1ded51692e1
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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