Pyridine → HCID 66879863, compound

HRID 2094439Notes

Reaction equation

HRID 2094439 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[OH:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5922Isonicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1202462-Amino-4-(trifluoromethyl)phenol

Product 1

HCID 66879863HCID 66879863, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.84 g of 2-amino-4-trifluoromethylphenol, 1.97 g of isonicotinic acid, 3.69 g of WSC [1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride] and 20 ml of pyridine was stirred while heating at 80° C. for four hours. The reaction mixture was cooled to room temperature, and then water was poured, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was washed with an ethyl acetate-hexane mixture solvent to give 1.69 g of N-(2-hydroxy-5-trifluoromethylphenyl)isonicotinamide.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with an ethyl acetate-hexane mixture solvent

Sources & evidence

ORD record
ord-5a175d557afa4bbab28451fc00558d04
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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