HCID 67834847, compound → HCID 14303549, compound

HRID 2350958Notes

Reaction equation

HRID 2350958 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[NH:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:6][C:7](=[O:18])[CH:8]([CH3:17])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[N:4]1[C:5]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:6][C:7](=[O:18])[C:8]([CH3:17])=[C:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 67834847HCID 67834847, compound

Product 1

HCID 14303549HCID 14303549, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 17.8 g (0.050 mole) of 5-(2-chloroanilino)-2-methyl-1,5-diphenyl-4-pentene-1,3-dione, 200 ml of xylene and 100 g of polyphosphoric acid were added. The resultant mixture was heated under reflux for 30 minutes. After cooling the reaction mixture, the solvent was removed by decantation and the remaining solid matter was added with 200 ml of chloroform and 200 ml of water. The resultant mixture was then stirred vigorously for 2 hours. Thereafter, the organic layer was washed with water and then dried over anhydrous sodium sulfate. After removal of the sodium sulfate, the solvent was distilled off and the residue was recrystallized from acetone, thereby affording 2.8 g of 1-(2-chlorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 228°-231° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureAfter cooling the reaction mixture
  3. customthe solvent was removed by decantation
  4. additionthe remaining solid matter was added with 200 ml of chloroform and 200 ml of water
  5. washThereafter, the organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the sodium sulfate
  8. distillationthe solvent was distilled off
  9. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-eaddbf2e9a564d1da00ffd81344435a9
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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