Sulfuric Acid → HCID 67834297, compound

HRID 845306Notes

Reaction equation

HRID 845306 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH3:10].[C:18]1([C:24]#[C:25][C:26]([O:28]CC)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-:31].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[ClH:31].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:25][C:26](=[O:28])[C:9]=1[CH3:10].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:25][C:26](=[O:28])[C:9]=1[CH3:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 19847706HCID 19847706, compound

Product 1

HCID 67834297HCID 67834297, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To 300 ml of toluene were added 6.4 g (0.022 mole) of 1-(2-bromophenyl)-N-phenylpropaneimine, 3.9 g (0.022 mole) ethyl phenylpropiolate and 3.6 g (0.027 mole) of aluminum chloride. The reaction mixture was then heated at 60° C. hours. After cooling, the reaction mixture was poured into 500 ml of 2N sulfuric acid, followed by extraction with methylene chloride. After washing the organic layer (the extract) with water, the organic layer was dried over anhydrous 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 then recrystallized from a 2:1 mixed solvent of acetone and hexane to obtain 1.3 g of 2-(2-bromophenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone hemihydrochloride having a melting point of 236°-238° C.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with methylene chloride
  3. washAfter washing the organic layer (the
  4. extractionextract) with water
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customThe resultant crystals were then recrystallized from a 2:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-672ab9507bc5434d9e4f845bf1ce19ad
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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