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

HRID 1283408Notes

Reaction equation

HRID 1283408 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[Cl:13][CH2:14][C:15]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:12])[NH:10]2)=[O:16]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 2682398-Hydroxy-3,4-dihydroquinolin-2(1h)-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 135332285-Chloroacetyl-8-hydroxy-3,4-dihydrocarbostyrilYield 37.7%

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 for 15 hours at a temperature of 70° to 75°C. The mixture was then steam-distilled to remove nitrobenzene. 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 mixture was then steam-distilled
  2. customto remove nitrobenzene
  3. temperatureto cool
  4. filtrationthe precipitated crystals were filtered
  5. washwashed with hot water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-95fd00febbf546c6b5a5762fab1e53b0
Source dataset
uspto-grants-1976_08
Patent number
US03975391

Reaction notes

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