Aniline → HCID 14303548, compound

HRID 845293Notes

Reaction equation

HRID 845293 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10](=O)[CH:11]([CH3:23])[C:12](=[O:22])[CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CS(O)(=O)=O>C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][C:12](=[O:22])[C:11]=2[CH3:23])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 6395Methanesulfonic AcidHCID 14303547HCID 14303547, compound

Product 1

HCID 14303548HCID 14303548, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 500 ml of xylene were dissolved 15.0 g (0.046 mole) of 1-(3-ethoxyphenyl)-2-methyl-5-phenyl-1,3,5-pentanetrione, 43.0 g (0.47 mole) of aniline and 8.8 g (0.092 mole) of methanesulfonic acid. The reaction mixture was heated under reflux for 30 minutes in a reactor fitted with a Dean-Stark apparatus. After cooling, the reaction mixture was filtered to remove solid matter, followed by removal of the solvent by distillation. The residue was extracted with chloroform and the resultant solution in chloroform (the extract) was washed first with 100 ml of 10% hydrochloric acid and then with 100 ml of a 10% aqueous solution of sodium hydroxide. The chloroform solution was washed further with water and 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). Upon recrystallization of the resultant crystals from acetone, 5.3 g of 2-(3-ethoxyphenyl)-3-methyl-1,6-diphenyl-4-(1H)-pyridinone having a melting point of 146°-149° C. was obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 30 minutes in a reactor
  3. customfitted with a Dean-Stark apparatus
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered
  6. customto remove solid matter
  7. customfollowed by removal of the solvent by distillation
  8. extractionThe residue was extracted with chloroform
  9. extractionthe resultant solution in chloroform (the extract)
  10. washwas washed first with 100 ml of 10% hydrochloric acid
  11. washThe chloroform solution was washed further with water
  12. dry with materialwas then dried over anhydrous sodium sulfate
  13. customSubsequent to removal of the sodium sulfate
  14. distillationthe solvent was distilled off
  15. customUpon recrystallization of the resultant crystals from acetone, 5.3 g of 2-(3-ethoxyphenyl)-3-methyl-1,6-diphenyl-4-(1H)-pyridinone having a melting point of 146°-149° C.
  16. customwas obtained

Sources & evidence

ORD record
ord-345937d7f2264d4a94d13565a2244181
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

Loading…