Sulfuric Acid → 1-(2-Chlorophenyl)-3-ethyl-2,6-diphenylpyridin-4(1H)-one

HRID 845304Notes

Reaction equation

HRID 845304 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10]CC.[C:19]1([C:25]#[C:26][C:27]([O:29]CC)=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O.[C:41]1(C)C=CC=C[CH:42]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:27](=[O:29])[C:26]([CH2:41][CH3:42])=[C:25]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 19847714HCID 19847714, compound

Product 1

HCID 143036971-(2-Chlorophenyl)-3-ethyl-2,6-diphenylpyridin-4(1H)-one

Procedure

To 300 ml of toluene were added 10.3 g (0.040 mole) of N-(2-chlorophenyl)-1-phenylbutaneimine, 5.2 g (0.030 mole) of ethyl phenylpropiolate and 5.3 g (0.040 mole) of aluminum chloride. After heating the reaction mixture under reflux for 20 hours under a nitrogen atmosphere, the reaction mixture was poured into 500 ml of 2N sulfuric acid which had been ice-cooled, followed by extraction with chloroform. After washing the organic layer with 50 ml of a 10% aqueous solution of sodium hydroxide and then with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) so that 2.0 g of 1-(2-chlorophenyl)-3-ethyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 165°-166° C. was obtained.

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperatureunder reflux for 20 hours under a nitrogen atmosphere
  3. temperaturecooled
  4. extractionfollowed by extraction with chloroform
  5. washAfter washing the organic layer with 50 ml of a 10% aqueous solution of sodium hydroxide
  6. dry with materialwith water, it was dried over anhydrous sodium sulfate
  7. customSubsequent to removal of the sodium sulfate
  8. distillationthe solvent was distilled off
  9. customthe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) so that 2.0 g of 1-(2-chlorophenyl)-3-ethyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 165°-166° C.
  10. customwas obtained

Sources & evidence

ORD record
ord-37c248f228b64cfeb26a571efbe5349d
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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