Methyl 2-amino-5-chloro-3-nitrobenzoate → Methyl 2,3-diamino-5-chlorobenzoate

HRID 1470623Notes

Reaction equation

HRID 1470623 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Cl: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]([Cl:10])[CH:7]=[C:6]([NH2:11])[C:5]=1[NH2:14]

Participants

5

Reactant 2

HCID 615489Methyl 2-amino-5-chloro-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58073866Methyl 2,3-diamino-5-chlorobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of 2-amino-5-chloro-3-nitro-benzoic acid methyl ester (1.8 g, 8.40 mmol) and 10% Pd/C (0.5 g) in methanol (50 mL) was hydrogenated with a hydrogen balloon for 2 h. After completion of reaction, the reaction mixture was filtered over a celite bed and concentrated to dryness. The resulting residue was purified by column chromatography using 30% ethyl acetate in hexane to obtain the title compound as off white solid.

Workup

  1. customAfter completion of reaction
  2. filtrationthe reaction mixture was filtered over a celite bed
  3. concentrationconcentrated to dryness
  4. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-fd8db01507f7422c851d0661009d180b
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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