Methyl vinyl ketone → HCID 23362108, compound

HRID 1082092Notes

Reaction equation

HRID 1082092 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:10].[CH3:11][C:12](=O)[CH:13]=[CH2:14]>C(O)C.[Fe](Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[Cl:9][C:8]1[C:3]([Cl:2])=[C:4]2[C:5]([C:13]([CH3:14])=[CH:12][CH:11]=[N:10]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 89987Benzenamine, 2,3-dichloro-, hydrochloride

Product 1

HCID 23362108HCID 23362108, compound

Reagents, catalysts & solvents 3

HCID 24380Iron chloride (FeCl3)CatalystHCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of 2,3-dichlorobenzenamine monohydrochloride (0.308 mol), iron(III) chloride (0.52 mol) and zinc chloride (0.0308 mol) in ethanol (800 ml) was heated at 65° C. for 30 minutes. 3-butenone (0.308 mol) in ethanol (200 ml) was added dropwise at 65° C. over a 1 hour period and the mixture was stirred and refluxed overnight. The mixture was cooled to room temperature and evaporated. The residue was taken up in water, basified with NH4OH, filtered off and extracted with ethyl acetate. The organic layer was extracted with 3N HCl. The aqueous layer was basified with NH4OH and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated, yielding 38g (58%) of 7,8-dichloro-4-methylquinoline (interm. 1).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled to room temperature
  3. customevaporated
  4. filtrationfiltered off
  5. extractionextracted with ethyl acetate
  6. extractionThe organic layer was extracted with 3N HCl
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-9fb6c04f341b43c59f2d14de100d42dc
Source dataset
uspto-grants-1996_12
Patent number
US05589484

Reaction notes

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