Chloroacetyl chloride → 5-(Chloroacetyl)-8-methoxy-1-methylquinolin-2(1H)-one

HRID 2397582Notes

Reaction equation

HRID 2397582 reaction equation
[N+](C1C=CC=CC=1)([O-])=O.[Cl:10][CH2:11][C:12](Cl)=[O:13].[CH3:15][N:16]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[O:27][CH3:28])[CH:20]=[CH:19][C:17]1=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:15][N:16]1[C:26]2[C:21](=[C:22]([C:12](=[O:13])[CH2:11][Cl:10])[CH:23]=[CH:24][C:25]=2[O:27][CH3:28])[CH:20]=[CH:19][C:17]1=[O:18]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 7416NitrobenzeneHCID 7427918-METHOXY-1-METHYL-1H-QUINOLIN-2-ONEHCID 6451240Aluminum(III) Chloride

Product 1

HCID 135332255-(Chloroacetyl)-8-methoxy-1-methylquinolin-2(1H)-one

Procedure

40 ml of nitrobenzene and 12 ml of monochloroacetyl chloride (V) were added to 7.4 g of 1-methyl-8-hydroxycarbostyril (VI), and 20 g of aluminum chloride was added slowly to the mixture while cooling with ice-water followed by allowing the mixture to react at a temperature of 60° C. for 18 hours while stirring. The reaction mixture was then poured into 500 ml of ice-water to precipitate the product. The precipitate was filtered, washed with diethyl ether and recrystallized from a mixture of ethanol and dimethylformamide (1:1 by volume) to obtain 2.8 g of white amorphous 1-methyl-5-chloroacetyl-8-hydroxycarbostyril (IV) having a melting point of 287° to 289° C. (with decomposition). The product thus obtained was confirmed by elemental analysis and IR and NMR spectral analyses.

Workup

  1. additionwas added slowly to the mixture
  2. customto react at a temperature of 60° C. for 18 hours
  3. customto precipitate the product
  4. filtrationThe precipitate was filtered
  5. washwashed with diethyl ether
  6. customrecrystallized from a mixture of ethanol and dimethylformamide (1:1 by volume)

Sources & evidence

ORD record
ord-0a67f48cfb45466793bef58e0e2f4133
Source dataset
uspto-grants-1977_05
Patent number
US04022784

Reaction notes

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