Acetic Acid → 5-Hydroxy-2-((2-methyl-3-(trifluoromethyl)phenyl)amino)-3-pyridinecarboxylic acid

HRID 1395648

Reaction equation

HRID 1395648 reaction equation
[CH3:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].C(O)(=[O:24])C.OO>O>[OH:24][C:11]1[CH:12]=[N:13][C:5]([NH:4][C:3]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([F:19])([F:21])[F:20])[C:2]=2[CH3:1])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 38081Flunixin

Product 1

HCID 129782155-Hydroxy-2-((2-methyl-3-(trifluoromethyl)phenyl)amino)-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 10 g. of 2-(2-methyl-3-trifluoromethylanilino) nicotinic acid and 160 ml. of glacial acetic acid, add 9 ml. of 30% hydrogen peroxide solution at room temperature. Warm the reaction mixture on a steam bath for one hour and add an additional 5 ml. of 30% hydrogen peroxide. Heat the resulting mixture for three hours on a steam bath, dilute with water and filter. After recrystallization from acetic acid, the product, 5-hydroxy-2-(2-methyl-3-trifluoromethylanilino) nicotinic acid melts at 305°-308° (dec.)

Workup

  1. additionTo a suspension of 10 g
  2. customat room temperature
  3. temperatureWarm the reaction mixture on a steam bath for one hour
  4. additionadd an additional 5 ml
  5. temperatureHeat the resulting mixture for three hours on a steam bath
  6. filtrationfilter
  7. customAfter recrystallization from acetic acid

Sources & evidence

ORD record
ord-d6cf29cb4a114fc897e812715c781ee1
Source dataset
uspto-grants-1980_05
Patent number
US04205073

Linked notes

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