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

HRID 1649005Notes

Reaction equation

HRID 1649005 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH:6]([CH3:10])[C:7](Cl)=[O:8].[NH:11]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][C:12]1=[O:13]>C(=S)=S>[Br:5][CH:6]([CH3:10])[C:7]([C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[NH:11][C:12](=[O:13])[CH2:14][CH2:15]2)=[O:8]

Participants

5

Reactant 3

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

Product 1

HCID 130510676-(2-Bromopropanoyl)-3,4-dihydroquinolin-2(1H)-oneYield 92.6%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of aluminum chloride (44 g) and α-bromopropionyl chloride (43 g) in carbon disulfide (150 ml) was added portionwise 3,4-dihydrocarbostyril (8 g) while refluxing with stirring. After completion of addition, the mixture was refluxed with stirring for 2 hours. After cooling, the mixture was poured into ice water and crystals which precipitated were collected by filtration and washed with water. Recrystallization from ethanol gave 14.2 g of 6-(α-bromopropionyl)-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. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-b39925a2b4bc4f49b2776fcb51ae0af1
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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