5-Amino-2-chlorobenzoic acid → 2-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acid

HRID 1662800Notes

Reaction equation

HRID 1662800 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18]>C1COCC1>[F:12][C:13]([F:23])([F:24])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])=[O:18]

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 534011722-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acidYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5-amino-2-chlorobenzoic acid (1.74 g, 10.1 mmol) in anhydrous THF (60 mL), 3-(trifluoromethyl)benzoyl chloride (2.33 g, 11.2 mmol) was added slowly. The mixture was stirred at room temperature under argon for overnight. The solvent was removed under reduced pressure and re-crystallized from acetone/chloroform (v/v 1:1) to afford the title compound as a white solid (1.5 g, 43%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customre-crystallized from acetone/chloroform (v/v 1:1)

Sources & evidence

ORD record
ord-8b4cd6d74cd44d289254fc7c4cdc9af0
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

Loading…