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

HRID 350572Notes

Reaction equation

HRID 350572 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) δ 2.23 (s, 3 H), 3.82 (s, 3H), 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-aafced9513c243d6bccbb064d94a6b6d
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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