6-Methyl-2-nitrobenzoic acid → 6-Methylanthranilic acid

HRID 1291213Notes

Reaction equation

HRID 1291213 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([N+:11]([O-])=O)[CH:5]=[CH:4][CH:3]=1>[Pd]>[NH2:11][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 160976-Methyl-2-nitrobenzoic acid

Product 1

HCID 1512106-Methylanthranilic acidYield 127.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a methanolic solution (150 ml) of 6-methyl-2-nitrobenzoic acid (14.25 g) was added palladium-on-carbon (1.40 g) and the hydrogenation reaction was conducted at atmospheric temperature and pressure (hydrogen consumption 5.3 1). The catalyst was filtered off and the filtrate was concentrated under reduced pressure to provide the title compound as light-yellow solid (15.12 g; yield 100%). 1H-NMR (CDCl3) δ: 2.47(3H,s), 6.50(2H,t,J=8.1Hz), 7.00-7.07(4H,m).

Workup

  1. customthe hydrogenation reaction
  2. customwas conducted at atmospheric temperature and pressure (hydrogen consumption 5.3 1)
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c3818b6ca8e4a70a671184c8c3b560c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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