Chloroform → HCID 10015445, compound

HRID 1647474Notes

Reaction equation

HRID 1647474 reaction equation
[C:1]([C:6]1[C:7](=O)[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]=[CH2:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH:19](Cl)(Cl)[Cl:20]>P(Cl)(Cl)(Cl)=O>[Cl:20][CH3:19].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:20])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]=[CH2:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 19923019HCID 19923019, compound

Product 2

HCID 6327Methyl ChlorideHCID 10015445HCID 10015445, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-Butyryl-8-vinylquinolone (23 g, 95 mmol) was heated under reflux in a mixture of phosphoryl chloride (100 ml) and chloroform (100 ml) for 45 minutes. The solvent was evaporated and the residue was mixed with ice, neutralized with ammonia solution and extracted into dichloromethane. The organic solution was washed successively with sodium hydrogen carbonate solution and brine, dried (anhyd. MgSO4), filtered and evaporated. Chromatography (silica gel, 2% methanol in di.chloromethane) afforded 3-butyryl-4-chloro-8-vinylquinoline as a brown oil (9.5 g, 38.5%).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was mixed with ice
  3. extractionextracted into dichloromethane
  4. washThe organic solution was washed successively with sodium hydrogen carbonate solution and brine
  5. dry with materialdried (anhyd. MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8fe1d62d81c44e1fb6d95f8dfa5713cf
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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