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

HRID 1981297Notes

Reaction equation

HRID 1981297 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:2]1=[O:3].[Cl:12][CH2:13][C:14](Cl)=[O:15].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:12][CH2:13][C:14]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[NH:1][C:2](=[O:3])[CH2:4][CH2:5]2)=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 64796HydrocarbostyrilHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

In to a mixture of 200 g of 3,4-dihydrocarbostyril, 160 ml of chloroacetylchloride and 300 ml of carbon disulfide, which was ice-cooled and stirred, 460 g of anhydrous pulverized aluminium chloride was added slowly at a temperature of the reaction vessel being kept within the range of from 5° to 15° C. After the addition of aluminium chloride was completed, the reaction mixture was refluxed for 40 minutes under stirring. The carbon disulfide was removed by decantation, then the residue obtained was poured into a large amount of ice-water and the crystals thus formed was collected by filtration, and washed with water well. The crystals was washed with methanol, dried then 280 g of 6-(2-chloroacetyl)-3,4-dihydrocarbostyril was obtained. Recrystallized from ethanol to obtain a colorless needle-like crystals. Melting point: 230°-231° C.

Workup

  1. temperaturecooled
  2. additionwas added slowly at a temperature of the reaction vessel
  3. custombeing kept within the range of from 5° to 15° C
  4. temperaturethe reaction mixture was refluxed for 40 minutes
  5. stirringunder stirring
  6. customThe carbon disulfide was removed by decantation
  7. customthe residue obtained
  8. customthe crystals thus formed
  9. filtrationwas collected by filtration
  10. washwashed with water well
  11. washThe crystals was washed with methanol
  12. customdried

Sources & evidence

ORD record
ord-b202c98543be48b995962c83fde4d74b
Source dataset
uspto-grants-1985_04
Patent number
US04514401

Reaction notes

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