Sulfuric Acid → HCID 14303792, compound

HRID 2350961Notes

Reaction equation

HRID 2350961 reaction equation
[C:1]1([N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[C:25][C:26]([O:28]CC)=O.[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:10])[C:26](=[O:28])[CH:25]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6451240Aluminum(III) ChlorideHCID 10397588Ethyl 3-(2-methylphenyl)prop-2-ynoateHCID 10899855HCID 10899855, compound

Product 1

HCID 14303792HCID 14303792, compoundYield 3.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To 300 ml of toluene were added 7.5 g (0.036 mole) of N-phenyl-1-phenylpropaneimine, 5.8 g (0.031 mole) of ethyl 2-methylphenylpropiolate and 6.0 g (0.045 mole) of aluminum chloride. The reaction mixture was stirred with heating at 60° C. for 3 days in a nitrogen atmosphere. After cooling, the reaction mixture was poured into 500 ml of 2N sulfuric acid, followed by extraction with chloroform. After washing the organic layer 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). The resultant crystals were washed with a 2:1 mixed solvent of acetone and hexane to obtain 0.4 g of 6-(2-methyl-phenyl)-3-methyl-1,2-diphenyl-4(1H)-pyridinone having a melting point of 188°-191° C.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with chloroform
  3. washAfter washing the organic layer with water, it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customSubsequent to removal of the sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)
  8. washThe resultant crystals were washed with a 2:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-6abea9daf25c40219ea9a7c93fb8681d
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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