Propanoyl bromide, 2-bromo- → 6-(2-Bromo-1-oxopropyl)-8-chloro-3,4-dihydro-2(1H)-quinolinone

HRID 1649007Notes

Reaction equation

HRID 1649007 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[NH:20][C:19](=[O:22])[CH2:18][CH2:17]2>C(=S)=S>[Cl:11][C:12]1[CH:13]=[C:14]([C:3](=[O:4])[CH:2]([Br:1])[CH3:6])[CH:15]=[C:16]2[C:21]=1[NH:20][C:19](=[O:22])[CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) ChlorideHCID 131049148-Chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 130510666-(2-Bromo-1-oxopropyl)-8-chloro-3,4-dihydro-2(1H)-quinolinoneYield 68.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of α-bromopropionyl bromide (60 g) and aluminum chloride (40 g) in carbon disulfide (100 ml) was added 8-chloro-3,4-dihydrocarbostyril (10 g). After refluxing the mixture for 5 hours, carbon disulfide was evaporated and heated at 70° to 80° C. for 5 hours. The reaction mixture was poured into ice water and allowed to stand overnight. The mixture was extracted with chloroform and the chloroform layer was washed with water, dried and treated with activated carbon followed by evaporating chloroform. The residue was washed with diethyl ether and collected by filtration. The residue gave uniform crude crystals upon TLC. The crystals thus obtained were re-crystallized from methanol to give 12 g of 8-chloro-6-α-bromopropionyl-3,4-dihydrocarbostyril.

Workup

  1. temperatureAfter refluxing the mixture for 5 hours
  2. customcarbon disulfide was evaporated
  3. temperatureheated at 70° to 80° C. for 5 hours
  4. additionThe reaction mixture was poured into ice water
  5. extractionThe mixture was extracted with chloroform
  6. washthe chloroform layer was washed with water
  7. customdried
  8. additiontreated with activated carbon
  9. customby evaporating chloroform
  10. washThe residue was washed with diethyl ether
  11. filtrationcollected by filtration
  12. customThe residue gave uniform crude crystals upon TLC
  13. customThe crystals thus obtained
  14. customwere re-crystallized from methanol

Sources & evidence

ORD record
ord-7242d23bb86d4e12a464e9db1ba5c78a
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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