5-Methoxy-2-nitrobenzoic acid → 5-Methoxyanthranilic acid

HRID 1520315Notes

Reaction equation

HRID 1520315 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9]>C1COCC1.[Pd]>[NH2:12][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 3392095-Methoxy-2-nitrobenzoic acid

Product 1

HCID 2779305-Methoxyanthranilic acidYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Methoxy-2-nitrobenzoic acid (30.0 g, 152.2 mmol) was hydrogenated over Pd/C (10% c, 300 mg) in THF (250 mL) at room temperature under H2 balloon. The mixture was stirred for 18 h. After the reaction was completed, the catalyst was removed by filtration over Celite and the filtrate was concentrated to afford 25.0 g of 2-amino-5-methoxybenzoic acid as a brown solid (98%). LCMS m/z=168.1 (M+1), 150.1 (M−17) (Method B) (retention time=0.53 min) 1H NMR (400 MHz, DMSO-d6): δ 7.31 (d, J=2.8 Hz, 1H), 6.61 (dd, J=8.8, 3.2 Hz, 1H), 6.44 (d, J=8.8 Hz, 1H), 3.60 (s, 3H).

Workup

  1. customthe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e764d83aeb954c11bd533f78871c5b92
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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