Pyridine → N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide

HRID 884927Notes

Reaction equation

HRID 884927 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[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]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[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 155242772-Amino-5-(trifluoromethyl)phenol

Product 1

HCID 66881414N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamideYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.30 g of 2-amino-5-trifluoromethylphenol, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80° C. for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customPrecipitated solid
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-49f26504f0424fcda4fb4ead33d952e2
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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