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

HRID 1470655Notes

Reaction equation

HRID 1470655 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].[H][H]>CO.[Pd]>[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

5

Reactant 2

HCID 607264Methyl 2-amino-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl esterYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 2-amino-3-nitro-benzoic acid methyl ester (2 g, 10 mmol) in methanol, a suspension of 10% Pd/C (300 mg) in methanol 5 mL was added and hydrogenated with a hydrogen balloon over a period of 8 h. The reaction mass was filtered and the filtrate was concentrated under reduced pressure to obtain 1.5 g of the required compound as a brown coloured solid (88%).

Workup

  1. additionwas added
  2. filtrationThe reaction mass was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bdbc977affb54770afffddde072d0299
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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