Methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate → Methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate

HRID 2262004Notes

Reaction equation

HRID 2262004 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[O:9])=[CH:4][C:3]=1[N+:20]([O-])=O>[Pd]>[NH2:20][C:3]1[CH:4]=[C:5]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[O:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

3

Reactant 1

HCID 14994663Methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate

Product 1

HCID 67044285Methyl 2-[(3,4-diaminophenyl)carbonyl]benzoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate (420 mg, 1.39 mmol) in a mixture of terahydrofuran-ethyl acetate (1:1, 20 mL) was hydrogenated over 10% Pd—C (10 mg) for 18 h. The catalyst removed by filtration and the filtrate concentrated to give methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate (370 mg, 98%) as a brown powder. MS (EI) for C15H14N2O3: 293 (M+Na).

Workup

  1. customThe catalyst removed by filtration
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-112eff7517a94e4ab33cb00902bfae8c
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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