2-(5-chloro-2-nitrophenylmethyl)benzoic Acid Methyl Ester → 2-(2-amino-5-chlorophenylmethyl)benzoic Acid Methyl Ester

HRID 50144Notes

Reaction equation

HRID 50144 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-])=O>C(O)(=O)C.O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[NH2:18]

Participants

3

Reactant 1

HCID 213015592-(5-chloro-2-nitrophenylmethyl)benzoic Acid Methyl Ester

Product 1

HCID 120966522-(2-amino-5-chlorophenylmethyl)benzoic Acid Methyl EsterYield 47.9%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To a solution of 2-(2-nitro-5-chlorophenylmethyl) benzoic acid methyl ester (840 mg; prepared in reference example 3) in a mixture of acetic acid-water (5:1; 12 ml) was added steel powder (768 mg) and the mixture was added for 20 minutes at 80° C. The suspension was poured into ice-water and was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried, and was concentrated. The residue was purified by column chromatography on silica gel to give the title compound (363 mg) having the following physical data.

Workup

  1. additionthe mixture was added for 20 minutes at 80° C
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried
  5. concentrationwas concentrated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-694ae5d4bfeb4d09a7f47bf569145a22
Source dataset
uspto-grants-2004_03
Patent number
US06710205B2

Reaction notes

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