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

HRID 2196477Notes

Reaction equation

HRID 2196477 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-fbdc46b66c6c49b59e96d9d0f5c776ff
Source dataset
uspto-grants-2012_12
Patent number
US08338459B2

Reaction notes

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