Hydrocarbostyril → 6-(2-Bromopropanoyl)-3,4-dihydroquinolin-2(1H)-one

HRID 620010Notes

Reaction equation

HRID 620010 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH:7]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][C:8]1=[O:9].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[NH:7][C:8](=[O:9])[CH2:10][CH2:11]2)=[O:4]

Participants

5

Reactant 3

HCID 64796HydrocarbostyrilHCID 979802-Bromopropanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130510676-(2-Bromopropanoyl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of α-bromopropionyl chloride (50 g) in methylene chloride (350 ml) is added to a stirred mixture of 3,4-dihydrocarbostyril (21.8 g) and aluminum chloride (44.8 g). The reaction mixture is stirred under reflux for four hours, poured into an ice water mixture, stirred for 30 minutes and the solid filtered, washed with water, dried, and recrystallized from isopropanol affording the desired product.

Workup

  1. temperatureunder reflux for four hours
  2. stirringstirred for 30 minutes
  3. filtrationthe solid filtered
  4. washwashed with water
  5. customdried
  6. customrecrystallized from isopropanol affording the desired product

Sources & evidence

ORD record
ord-78322a2474f6437bb2a5d571f3876d2e
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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