Chloroacetyl chloride → 5-Chloroacetyl-8-methoxy-3,4-dihydrocarbostyril

HRID 1834071Notes

Reaction equation

HRID 1834071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[Cl:14][CH2:15][C:16](Cl)=[O:17].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[Cl:14][CH2:15][C:16]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:13])[NH:11]2)=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 133754763,4-Dihydro-8-methoxy-2(1H)-quinolinone

Product 1

HCID 135332315-Chloroacetyl-8-methoxy-3,4-dihydrocarbostyrilYield 38.7%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

13 g of 8-hydroxy-3,4-dihydrocarbostyril (VII) and 20 g of chloroacetyl chloride were dissolved in 100 ml of nitrobenzene, and 40 g of aluminum chloride was added slowly to the mixture followed by stirring at a temperature of 70° to 75° C for 15 hours. The nitrobenzene was then steam-distilled. After allowing the mixture to cool, the precipitated crystals were filtered, washed with hot water and recrystallized from methanol to give 7.2 g of 5-chloroacetyl-8-hydroxy-3,4-dihydrocarbostyril (IV) as light yellow crystals having a melting point of 189° to 190° C.

Workup

  1. distillationThe nitrobenzene was then steam-distilled
  2. temperatureto cool
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with hot water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5ba8407c427d481baa63847aabc1b246
Source dataset
uspto-grants-1978_01
Patent number
US04068076

Reaction notes

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