Water → HCID 20198099, compound

HRID 651908Notes

Reaction equation

HRID 651908 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[CH3:6][N:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19](F)(F)F)[CH:14]=2)[C:10](=[O:23])[C:9]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:8]1.[OH2:29]>>[C:19]([C:15]1[CH:14]=[C:13]([C:11]2[C:10](=[O:23])[C:9]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:8][N:7]([CH3:6])[CH:12]=2)[CH:18]=[CH:17][CH:16]=1)([OH:2])=[O:29].[S:1](=[O:3])(=[O:2])([OH:5])[OH:4]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13603717HCID 13603717, compound

Product 1

HCID 20198099HCID 20198099, compound

Conditions

Temperature
140 °C

Procedure

200 ml (3.74 moles) of concentrated sulphuric acid are added dropwise to 150 g (0.47 mole) of 1-methyl-3-(pyrazol-1-yl)-5-(3-trifluoromethylphenyl)-4-pyridone, with stirring, whereupon the temperature rises to 80° C. to 90° C. When the addition has ended, the mixture is warmed at 140° C., with stirring, until the evolution of gas has ended (about 45 minutes) and is then left to cool to about 40° C. to 50° C., 200 ml of water are carefully added in small portions and, when the addition has ended, the mixture is heated at the reflux temperature for about 60 minutes. The precipitate which separates out of the cooled reaction mixture is filtered off with suction, washed with a little water and dried at 80° C. 148 g (about 80% of theory) of a solid [5-(3-carboxyphenyl)-1-methyl-3-(pyrazol-1-yl)-4-pyridone-sulphuric acid adduct (xn H2SO4)] are obtained, 40 g of which (about 0.1 mole) are dissolved in a mixture of 700 ml of water and 700 ml of ethanol at 70° C. An aqueous barium hydroxide solution is added dropwise to this solution until the pH reaches 7.5, and the barium sulphate precipitated is filtered off with suction over kieselguhr. Solid carbon dioxide is added to the filtrate at room temperature until, at a pH value of 5.5, the free acid precipitates, which is filtered off with suction, washed with a little cold water and dried. 11.5 g (37% of theory) of 5-(3-carboxyphenyl)-1-methyl-3-(pyrazol-1-yl)-4-pyridone of melting point 280° C. are obtained.

Workup

  1. customrises to 80° C. to 90° C
  2. additionWhen the addition
  3. stirringwith stirring, until the evolution of gas
  4. custom(about 45 minutes)
  5. waitis then left
  6. temperatureto cool to about 40° C. to 50° C.
  7. additionthe addition
  8. temperaturethe mixture is heated at the reflux temperature for about 60 minutes
  9. customThe precipitate which separates out of the cooled reaction mixture
  10. filtrationis filtered off with suction
  11. washwashed with a little water
  12. customdried at 80° C

Sources & evidence

ORD record
ord-ef899ec038924d68a74bf0cdb5ce95ce
Source dataset
uspto-grants-1987_06
Patent number
US04670044

Reaction notes

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