Methyl 2-amino-3-nitrobenzoate → 2,3-Diaminobenzoic acid methyl ester

HRID 1445285Notes

Reaction equation

HRID 1445285 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH2:13]>[Pd].CCO>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:13]

Participants

4

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Amino-3-nitro benzoic acid methyl ester 1 (1.0 g, 5.1 mmol) and palladium on carbon (10%, 0.5 g) were mixed in EtOH (20 mL) and were hydrogenated at 15 psi for 1 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. The resulting solid was dried to give 0.73 g (86%) of pure 2: 1H NMR (CDCl3) δ 7.47 (d, 1H, J=8.0 Hz), 6.85 (d, 1H, J=6.5 Hz), 6.60 (t, 1H, J=8.0 Hz), 3.87 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting solid was dried
  4. customto give 0.73 g (86%) of pure 2

Sources & evidence

ORD record
ord-6bd55060703d4a7ca8b8af64e2382d3b
Source dataset
uspto-grants-2010_02
Patent number
USRE041150E1

Reaction notes

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