Methyl 2-amino-3-nitrobenzoate → 2,3-Diaminobenzoic acid methyl ester

HRID 1176560Notes

Reaction equation

HRID 1176560 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10.10 g of methyl 2-amino-3-nitrobenzoate are suspended in 250 ml of methanol. 10% Pd/C (1.08 g) is added under argon and the reaction mixture is hydrogenated at room temperature at atmospheric pressure over 3 hours. The catalyst is filtered off through Hyflo and the filtrate is concentrated by evaporation. The title compound is isolated as a brown solid. Rt=2.15.

Workup

  1. filtrationThe catalyst is filtered off through Hyflo
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-bce5d9551c7344ecb4239b20a9ef363b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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