Potassium Hydroxide → Diclofenac

HRID 894400Notes

Reaction equation

HRID 894400 reaction equation
[OH-:1].[K+].CN(C)[C:5](=[O:22])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21]>C(O)C>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[NH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][C:5]([OH:22])=[O:1]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 128842302-[2-(2,6-Dichloroanilino)phenyl]-N,N-dimethylacetamide

Product 1

HCID 3033DiclofenacYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 40 ml of a 15% ethanol solution of potassium hydroxide was added 1.7 g of N,N-dimethyl-o-(2,6-dichloroanilino)phenylacetamide, and the mixture was agitated under reflux for 4 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and 30 ml of water was added to the residue and the mixture was made acidic by hydrochloric acid at a temperature lower than 5° C. The precipitated crystal was recovered by filtration under suction, washed with water and dried. Recrystallization from a mixed solvent of ether and petroleum ether gave 1.45 g of a colorless crystal having a melting point of 158° to 160° C. The yield was 92.9%.

Workup

  1. temperatureunder reflux for 4 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation under reduced pressure, and 30 ml of water
  4. additionwas added to the residue
  5. customwas made acidic by hydrochloric acid at a temperature lower than 5° C
  6. filtrationThe precipitated crystal was recovered by filtration under suction
  7. washwashed with water
  8. customdried
  9. customRecrystallization from a mixed solvent of ether and petroleum ether

Sources & evidence

ORD record
ord-f2c56385b75741c3a3ca1797cfeaae2c
Source dataset
uspto-grants-1981_08
Patent number
US04283532

Reaction notes

Loading…