2-Hydroxyquinoline → 6-(Chloroacetyl)quinolin-2(1H)-one

HRID 1153978Notes

Reaction equation

HRID 1153978 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

5

Reactant 3

HCID 60382-HydroxyquinolineHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 128335076-(Chloroacetyl)quinolin-2(1H)-oneYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 467 g of chloroacetyl chloride in 400 ml of dichloromethane was added 735 g of aluminum chloride by way of one-third portion thereof in three times, at below 30° C., with stirring, then 200 g of the carbostyril was added to the mixture at the same temperature under stirring. Then the reaction mixture was refluxed for 6 hours. After the reaction was completed, the reaction mixture was poured into ice-concentrated hydrochloric acid and the crystals formed were collected by filtration, and washed with a hot methanol to obtain 153 g of 6-chloroacetylcarbostyril. The mother liquor was concentrated to dryness and the residue was purified by a silica gel column cromatography. Recrystallized from methanol to obtain 35.41 g of 8-chloroacetyl-carbostyril. Light yellow needle-like crystals. Melting point: 177.5°-179° C.

Workup

  1. stirringunder stirring
  2. temperatureThen the reaction mixture was refluxed for 6 hours
  3. additionthe reaction mixture was poured into ice-concentrated hydrochloric acid
  4. customthe crystals formed
  5. filtrationwere collected by filtration
  6. washwashed with a hot methanol

Sources & evidence

ORD record
ord-6896f7ebf7884d5f8047912d9ddc96e8
Source dataset
uspto-grants-1984_12
Patent number
US04487772

Reaction notes

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