2-Hydroxyquinoline → 6-(Chloroacetyl)quinolin-2(1H)-one
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[NH:10]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:11]1=[O:12]>ClCCl>[Cl:1][CH2:2][C:3]([C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[NH:10][C:11](=[O:12])[CH:13]=[CH:14]2)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution containing 467 g of chloroacetyl chloride in 400 ml of dichloromethan, 735 g of aluminium chloride was added by 1/3 each at a temperature below 30° C. with stirring condition. Next 200 g of carbostyril was added thereto at the same temperature under stirring condition. The reaction mixture was refluxed for 6 hours, then the reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid and the crystals formed were collected by filtration. The crystals were washed with methanol, then with hot-methanol to obtain 153 g of 6-chloroacetylcarbostyril. The mother liquor was concentrated to dryness, and the residue obtained was purified by a silica gel column chromatography, then recrystallized from methanol to obtain 35.41 g of 8-chloroacetylcarbostyril in the form of light yellow crystals.
Workup
- additionwas added by 1/3 each at a temperature below 30° C.
- stirringat the same temperature under stirring condition
- temperatureThe reaction mixture was refluxed for 6 hours
- additionthe reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid
- customthe crystals formed
- filtrationwere collected by filtration
- washThe crystals were washed with methanol
Sources & evidence
- ORD record
- ord-53195dca2bff49d49923c748f3aae8e6
- Source dataset
- uspto-grants-1994_09
- Patent number
- USRE034722
Reaction notes
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