Aniline → HCID 14303811, compound

HRID 2350953Notes

Reaction equation

HRID 2350953 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11](=[O:22])[CH:12]([CH3:21])[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)=[CH:5][CH:4]=1)#[N:2].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CS(O)(=O)=O.FC(F)(F)S(O)(=O)=O>C1(C)C(C)=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:12]([CH3:21])[C:11](=[O:22])[CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6395Methanesulfonic AcidHCID 62406Trifluoromethanesulfonic acidHCID 19847712HCID 19847712, compound

Product 1

HCID 14303811HCID 14303811, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 400 ml of xylene were dissolved 10.0 g (0.033 mole) of 5-(4-cyanophenyl)-2-methyl-1-phenyl-1,3,5-pentanetrione, 25.0 g (0.26 mole) of aniline and 7.0 g (0.073 mole) of methanesulfonic acid. The solution obtained was heated under reflux for 30 minutes in a reactor fitted with a Dean-Stark apparatus. After cooling, 6.5 g (0.043 mole) of trifluoromethanesulfonic acid was added further to the reaction mixture and the resultant mixture was similarly heated under reflux for 30 minutes. After cooling, solid matter was removed from the reaction mixture, followed by concentration under pressure. The concentrate was extracted with dichloromethane. The organic layer was washed successively with 100 ml of 10% hydrochloric acid, 100 ml of a 10% aqueous solution of sodium hydroxide and water. The organic layer was then dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was subjected to chromatography on a silica gel column (eluent: ethyl acetate). The resultant crystals were washed with acetone to afford 2.4 g of 6-(4-cyanophenyl)-3-methyl-1,2-diphenyl-4(1H)-pyridinone having a melting point of 229°-233° C.

Workup

  1. customThe solution obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 30 minutes in a reactor
  4. customfitted with a Dean-Stark apparatus
  5. temperatureAfter cooling
  6. temperatureunder reflux for 30 minutes
  7. temperatureAfter cooling
  8. customsolid matter was removed from the reaction mixture
  9. concentrationfollowed by concentration under pressure
  10. extractionThe concentrate was extracted with dichloromethane
  11. washThe organic layer was washed successively with 100 ml of 10% hydrochloric acid, 100 ml of a 10% aqueous solution of sodium hydroxide and water
  12. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  13. customSubsequent to removal of the sodium sulfate
  14. distillationthe solvent was distilled off
  15. washThe resultant crystals were washed with acetone

Sources & evidence

ORD record
ord-ada3ae333c3149aba849844c942c6366
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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