Methyl 3-methoxy-4-nitrobenzoate → Methyl 4-amino-3-methoxybenzoate

HRID 1177348Notes

Reaction equation

HRID 1177348 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:6]([O:8][CH3:9])=[O:7]>CO.[Ni]>[NH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Product 1

HCID 602411Methyl 4-amino-3-methoxybenzoateYield 86.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-methoxy-4-nitrobenzoate (172 g, 0.815 mol) in methanol (2 L) was added Raney Ni (60 g) in one portion. The resulting mixture was stirred at ambient temperature under H2 for 24 h. TLC (EtOAc: Petroleum ether 1:3) indicated the reaction was complete. The reaction mixture was filtered through a pad of Celite and the filter cake was washed with methanol (100 mL×5). The filtrate was concentrated in vacuum to afford the desired amine (128 g, 86.7%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.383-7.349 (dd, 1H), 7.268 (d, 1H), 6.633-6.605 (d, 1H), 5.617 (s, 2H), 3.782 (s, 3H), 3.740 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with methanol (100 mL×5)
  3. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-27807ce668da44bb91b1a749341f6371
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…