2-(4-Chloro-2-nitroanilino)benzoic acid → N-(2-Amino-4-chlorophenyl)anthranilic acid

HRID 16189Notes

Reaction equation

HRID 16189 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])=[C:4]([N+:18]([O-])=O)[CH:3]=1>C(OCC)(=O)C.[Pt]>[NH2:18][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 120423912-(4-Chloro-2-nitroanilino)benzoic acid

Product 1

HCID 610730N-(2-Amino-4-chlorophenyl)anthranilic acid

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(4-chloro-2-nitrophenyl)amino]benzoic acid (12.8 g, 43.7 mmol) in ethyl acetate (300 mL) was added platinum on sulfide coal 5%. The reaction mixture was hydrogenated at 2 bar for 5 h. After filtration through dicalite, washing with ethyl acetate and removal of the solvent under reduced pressure the title compound (11.8 g, 100%) was obtained.

Workup

  1. filtrationAfter filtration through dicalite
  2. washwashing with ethyl acetate and removal of the solvent under reduced pressure the title compound (11.8 g, 100%)
  3. customwas obtained

Sources & evidence

ORD record
ord-c106789049494f1291f6948194731277
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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