3-Aminobenzoic Acid → 3-(3-(Trifluoromethyl)Benzamido)Benzoic Acid

HRID 1662806Notes

Reaction equation

HRID 1662806 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>C1COCC1>[F:11][C:12]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])=[O:17]

Participants

4

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 454258443-(3-(Trifluoromethyl)Benzamido)Benzoic AcidYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3-aminobenzoic acid (1.1 g, 7.9 mmol) in anhydrous THF (20 mL), 3-(trifluoromethyl)benzoyl chloride (2.0 g, 9.6 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 chloroform to afford the title compound as a white solid (1.2 g, 49%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customre-crystallized from chloroform

Sources & evidence

ORD record
ord-e45a3d8d9766451fbd9907ab1220369d
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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