Nitrogen → 3-Amino-4-(methylamino)benzoic acid

HRID 412693Notes

Reaction equation

HRID 412693 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][CH3:14])[C:7]([OH:9])=[O:8])([O-])=O.N#N>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][CH3:14])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 947NitrogenHCID 2834754-(Methylamino)-3-nitrobenzoic acid

Product 1

HCID 115211443-Amino-4-(methylamino)benzoic acidYield 61.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

((b) Ethyl alcohol (100 mL) was added to a flask containing 3-nitro-4-methylaminobenzoic acid (2.09 g, 10.7 mmol) and 10% Pd/C (30 mg) under a steady stream of N2. The mixture was stirred under hydrogen for 16 hours, filtered through a milipore 0.22 μm type GV filter disc and concentrated on a rotary evaporator. The residue was dried under vaccum to provide 3-amino-4-methylaminobenzoic acid (1.1 g, 61% yield).

Workup

  1. filtrationfiltered through a milipore 0.22 μm type GV
  2. filtrationfilter disc
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue was dried under vaccum

Sources & evidence

ORD record
ord-234edffbacda42fc9ff9321150432bb9
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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