p-Toluenesulfonic acid → HCID 14304090, compound

HRID 845318Notes

Reaction equation

HRID 845318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([CH3:22])[C:10](=[O:21])[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])=O.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[CH:11][C:10](=[O:21])[C:9]=1[CH3:22]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 19847703HCID 19847703, compound

Product 1

HCID 14304090HCID 14304090, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 450 ml of xylene were suspended 15.3 g of 1-(2-chlorophenyl)-2-methyl-5-(2-fluoro-phenyl)-1,3,5-pentanetrione, 6.4 g of aniline, 6.6 g of para-toluenesulfonic acid and 85 g of Molecular Sieves 5A, followed by refluxing the resultant mixture for 8 hours. Xylene was distilled off from the reaction mixture and 300 ml of chloroform was added to the residue. The mixture obtained was filtered and the filtrate was washed first with 10% hydrochloric acid and then with a 10% aqueous solution of sodium hydroxide. After washing the chloroform phase further with water, the solution in chloroform was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate-n-hexane, 1:3) to afford crude crystals. The crystals were recrystallized from ethyl acetate, yielding 4.5 g of 2-(2-chlorophenyl)-6-(2-fluorophenyl)-3-methyl-1-phenyl-4(1H)-pyridinone having a melting point of 182°-183° C.

Workup

  1. distillationXylene was distilled off from the reaction mixture and 300 ml of chloroform
  2. additionwas added to the residue
  3. customThe mixture obtained
  4. filtrationwas filtered
  5. washthe filtrate was washed first with 10% hydrochloric acid
  6. washAfter washing the chloroform phase further with water
  7. dry with materialthe solution in chloroform was dried over anhydrous sodium sulfate
  8. customSubsequent to removal of the sodium sulfate
  9. distillationthe solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent: ethyl acetate-n-hexane, 1:3)
  11. customto afford crude crystals
  12. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-602c62aa943349e98b3ffb565b992210
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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