2-Amino-3-nitrobenzoic acid → 2,3-Diaminobenzoic acid

HRID 1870932Notes

Reaction equation

HRID 1870932 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>[Pd].CO>[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 1980692,3-Diaminobenzoic acidYield 67.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Palladium on carbon catalyst (10% Pd, ~200 mg) was added cautiously, as a slurry in methanol (10ml), to a solution of 3-nitroanthranilic acid (2.44 g, 13 mmol) in methanol (120 ml), and the mixture was stirred under a hydrogen atmosphere for 2 hours until the absorption of gas ceased. The catalyst was removed by filtration through Celite, and the filtrate was evaporated to dryness under reduced pressure to afford the crude product. Purification by column chromatography on silica gel, with dichloromethane:methanol (4:1) as eluent, gave 2,3-diaminobenzoic acid as a red solid (1.34 g, 66%). vmax /cm-1 3433.73, 2882.02, 2602.30 and 1658.99; δH (d6 -DMSO, 200 MHz) 5.8-7.4 (4H, br s, 2×NH2), 6.45 (1H, t, Ar-5H), 6.75 (1H, d, Ar-4H), 7.20 (1H, d, Ar-6H); δC (d6 -DMSO) 110.31, 115.45, 118.33, 120.55, 135.03, 140.36, 170.68; m/z (EI) 152 (M+), 134, 106, 79.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-ba641a763e394840abf9a23f39f8c39d
Source dataset
uspto-grants-2000_08
Patent number
US06100283

Reaction notes

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