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

HRID 1283407Notes

Reaction equation

HRID 1283407 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-]>C(=S)=S>[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 22.4%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

24.3 g of 8-hydroxy-3,4-dihydrocarbostyril (VII) and 68 g of chloroacetyl chloride were added to 130 ml of carbon disulfide, and 200 g of aluminum chloride was added slowly to the mixture while stirring and cooling in ice-water. The mixture was stirred for 6 hours at a temperature of 60° to 70°C and carbon disulfide was distilled off. The resulting residue was poured into 500 ml of ice-water. The precipitated crystals were filtered, washed with water and recrystallized twice from methanol to give 8.0 g of 5-chloroacetyl-8-hydroxy-3,4-dihydrocarbostyril (IV) as light yellow crystals having a melting point of 189° to 191°C.

Workup

  1. additionwas added slowly to the mixture
  2. distillationwas distilled off
  3. additionThe resulting residue was poured into 500 ml of ice-water
  4. filtrationThe precipitated crystals were filtered
  5. washwashed with water
  6. customrecrystallized twice from methanol

Sources & evidence

ORD record
ord-3bdda65e6a3842c0bf12d171fb2fe6ff
Source dataset
uspto-grants-1976_08
Patent number
US03975391

Reaction notes

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