Phosphorus oxychloride → HCID 10015445, compound

HRID 1534489Notes

Reaction equation

HRID 1534489 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].P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:21])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]=[CH2:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19923019HCID 19923019, compound

Product 1

HCID 10015445HCID 10015445, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Butyryl-8-vinylquinolone (23 g, 95 mmol) was heated under reflux in a mixture of phosphoryl chloride (I00 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 dichloromethane) 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-87cc208ea48249499d5dacbb25d83e69
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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