1-Bromo-3-chloropropane → 5-Chloro-1-(3-chloropropyl)-3,4-dihydrocarbostyril

HRID 2256982Notes

Reaction equation

HRID 2256982 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:14])[NH:9]2.Br[CH2:16][CH2:17][CH2:18][Cl:19]>CN(C=O)C>[Cl:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:14])[N:9]2[CH2:16][CH2:17][CH2:18][Cl:19]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 190277365-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 153840875-Chloro-1-(3-chloropropyl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the same manner as in Reference Example 1, 60% sodium hydride in oil was added portionwise to a solution of 5-chloro-3,4-dihydrocarbostyril in DMF, the resultant mixture was stirred for 30 minutes, 1-bromo-3-chloropropane was then added, and the resultant mixture was further stirred at 80°-90° C. for 8 hours. The DMF was distilled off under reduced pressure, and the residue was extracted with chloroform. The extract was washed with water and dried (anhydrous magnesium sulfate), the chloroform was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to give 5-chloro-1-(3-chloropropyl)-3,4-dihydrocarbostyril as a pale yellow oil.

Workup

  1. distillationThe DMF was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe chloroform was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-535407ebb61b41e0923bfe11451cdb65
Source dataset
uspto-grants-1997_08
Patent number
US05656633

Reaction notes

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