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

HRID 620009Notes

Reaction equation

HRID 620009 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH:6]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:7]1=[O:8].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:6][C:7](=[O:8])[CH2:9][CH2:10]2)=[O:4]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (64 g) is added to a stirred solution of 3,4-dihydrocarbostyril (40 g) and aluminum chloride (76 g) in methylene chloride (500 ml). The reaction mixture is refluxed for 3 hours, cooled to RT and poured into ice water affording a white solid which is filtered, washed with water, dried, and recrystallized from ethanol, yielding the desired product.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. filtrationis filtered
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-61b6ae5cf282427497da97b67ebcbb28
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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