Chloroacetyl chloride → 6-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one

HRID 1649006Notes

Reaction equation

HRID 1649006 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[NH:10]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:11]1=[O:12]>C(=S)=S>[Cl:5][CH2:6][C:7]([C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[NH:10][C:11](=[O:12])[CH2:13][CH2:14]2)=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 64796HydrocarbostyrilHCID 6451240Aluminum(III) Chloride

Product 1

HCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a solution of aluminum chloride (80 g) and chloroacetyl chloride (72 g) in carbon disulfide (200 ml) was added portionwise in 20 minutes a suspension of 3,4-dihydrocarbostyril (14.7 g) in carbon disulfide (100 ml) while refluxing with stirring. After completion of addition, the mixture was refluxed with stirring for 2 hours. After cooling, the reaction mixture was poured into ice water, and crystals which precipitated were collected by filtration, washed with water and recrystallized from ethanol to give 20 g of 6-chloroacetyl-3,4-dihydrocarbostyril.

Workup

  1. temperaturewhile refluxing
  2. additionAfter completion of addition
  3. temperaturethe mixture was refluxed
  4. stirringwith stirring for 2 hours
  5. temperatureAfter cooling
  6. customprecipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c2e780f9b31b4664bc072b17f32499dc
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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