Methyl 2-chloro-4-nitrobenzoate → Methyl 4-Amino-2-chlorobenzoate

HRID 417190Notes

Reaction equation

HRID 417190 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[Cl:13]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[Cl:13]

Participants

4

Reactant 1

HCID 83343Methyl 2-chloro-4-nitrobenzoate

Product 1

HCID 11839197Methyl 4-Amino-2-chlorobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitro-2-chlorobenzoic acid methyl ester (Aldrich, 700 mg, 3.24 mmol) in ethyl acetate (50 mL) was added 10% Pd/C (50 mg). The mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) for 3 h. The mixture was filtered through a short pad of celite and the filtrate was concentrated to give 4-amino-2-chlorobenzoic acid methyl ester as a light yellow solid which was directly used for the next step.

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d118d5eb890c4f1586ec969e65c7d70e
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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