Pyridine → 4-Hydroxy-3-(4-trifluoromethoxy-benzoylamino)-benzoic acid

HRID 252235

Reaction equation

HRID 252235 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].N1C=CC=CC=1.[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C1COCC1>[OH:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([O:20][C:19]([F:18])([F:30])[F:31])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 650833-Amino-4-hydroxybenzoic acidHCID 1421104-(Trifluoromethoxy)benzoyl Chloride

Product 1

HCID 600571974-Hydroxy-3-(4-trifluoromethoxy-benzoylamino)-benzoic acidYield 57.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-Amino-4-hydroxy benzoic acid (0.136, 0.00089 mols) and pyridine (0.211 g, 0.00267 mols) in 13 ml dry THF is added 4-trifluoromethoxybenzoyl chloride (0.2 g, 0.00089 mols) and the solution is stirred under nitrogen atmosphere at RT for 10 hrs and then refluxed for 3 hrs. The reaction mixture is rotary evaporated and the residue is slurried in water and filtered to get the amide (0.175 g) which is taken for the next step without further purification.

Workup

  1. temperaturerefluxed for 3 hrs
  2. customThe reaction mixture is rotary evaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2994cb0e83df417f9862d61358c83ade
Source dataset
uspto-grants-2011_01
Patent number
US07868033B2

Linked notes

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