4-(Methylamino)-3-nitrobenzoic acid → 3-Amino-4-(methylamino)benzoic acid

HRID 626240Notes

Reaction equation

HRID 626240 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[NH:2][CH3:1])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acid

Product 1

HCID 115211443-Amino-4-(methylamino)benzoic acidYield 36.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(methylamino)-3-nitrobenzoic acid (29 g, 1.0 eq) and Pd/C (5 g, 10%) in 300 mL MeOH was stirred at rt under hydrogen for 48 h and filtered. The filtrate was concentrated in vacuo to give the product (9 g, 36.5%). 1H NMR (400 MHz, DMSO-d6) δ 7.21 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.14 (d, J=2.0 Hz, 1H), 6.37 (d, J=8.4 Hz, 1H), 5.28 (brs, 1H), 4.60 (brs, 2H), 2.76 (s, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a4c1c8e05e20480bb1b309823f24fc53
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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