Methyl 2-amino-5-methyl-3-nitrobenzoate → Methyl 2,3-diamino-5-methylbenzoate

HRID 1470606Notes

Reaction equation

HRID 1470606 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[NH2:14].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([NH2:11])[C:5]=1[NH2:14]

Participants

5

Reactant 2

HCID 58213211Methyl 2-amino-5-methyl-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58073904Methyl 2,3-diamino-5-methylbenzoateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-amino-5-methyl-3-nitro-benzoic acid methyl ester (5.5 g, 26 mmol) in methanol (200 mL) was hydrogenated with hydrogen balloon in presence of 10% Palladium on charcoal (1.5 g) for 12 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to get the required product as a brown coloured solid 4.5 g (95%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ece7c9d96db04a6c941128cbe7859f93
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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