Hydrochloric Acid → 6-(4-Chloro-1-butenyl)-3,4-dihydrocarbostyril

HRID 1263102Notes

Reaction equation

HRID 1263102 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)=O.[BH4-].[Na+].Cl>CO>[Cl:1][CH2:2][CH2:3][CH:4]=[CH:5][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 128335166-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

Product 1

HCID 544375796-(4-Chloro-1-butenyl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.0 Grams of 6-(4-chloro-1-oxobutyl)-3,4-dihydrocarbostyril was disposed in 200 ml of methanol, and the suspension was stirred at a room temperature. Then 2.0 g of sodium borohydride was added to the suspension gradually and the reaction was continued for 1 hour. Next, 3 ml of concentrated hydrochloric acid was added to the reaction mixture and the mixture was concentrated under a reduce pressure with heat-refluxing condition to obtain a residue. The residue was extracted with chloroform and the chloroform layer was washed with water and dried. Then chloroform was removed by distillation under a reduced pressure to obtain a residue, and the residue was recrystallized from ethanol to obtain 2.4 g of 6-(4-chloro-1-butenyl)-3,4-dihydrocarbostyril in yellow needle-like crystals. Melting point: 153°-155° C.

Workup

  1. concentrationthe mixture was concentrated under a reduce pressure
  2. temperaturewith heat-refluxing condition
  3. customto obtain a residue
  4. extractionThe residue was extracted with chloroform
  5. washthe chloroform layer was washed with water
  6. customdried
  7. customThen chloroform was removed by distillation under a reduced pressure
  8. customto obtain a residue
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-195476a4c7084730b5a604f8341476c7
Source dataset
uspto-grants-1984_06
Patent number
US04455422

Reaction notes

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