5-Chloro-2-nitrobenzoic acid → 2-Amino-5-chlorobenzoic acid

HRID 654460Notes

Reaction equation

HRID 654460 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>O1CCCC1.[Rh]>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 124762-Amino-5-chlorobenzoic acidYield 80.8%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

8.0 g of 5-chloro-2-nitrobenzoic acid [4-(3-chloro-5-trifluoromethylpyridyl-2-oxy)-anilide] are dissolved in 90 ml of tetrahydrofuran and the solution is hydrogenated for 6 hours at room temperature under a hydrogen atmosphere in the presence of 4 g of 5% rhodium/carbon. The reaction mixture is then filtered and the solvent is removed by distillation. The resulting crude product is stirred with diethyl ether. 5.5 g of 2-amino-5-chlorobenzoic acid [4-(3-chloro-5-trifluoromethylpyridyl-2-oxy)-anilide] are obtained in the form of white crystals (m.p. 180°-184° C.).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-bfe272498c22487fba30183e4d73ae29
Source dataset
uspto-grants-1992_07
Patent number
US05132314

Reaction notes

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