Sodium borohydride → 6-(1-Hydroxy-4-chlorobutyl)-3,4-dihydrocarbostyril

HRID 1263101Notes

Reaction equation

HRID 1263101 reaction equation
[O:1]=[C:2]([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)[CH2:3][CH2:4][CH2:5][Cl:6].[BH4-].[Na+]>CO>[OH:1][CH:2]([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)[CH2:3][CH2:4][CH2:5][Cl:6]

Participants

4

Reactant 2

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

Product 1

HCID 128335136-(1-Hydroxy-4-chlorobutyl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 Grams of 6-(1-oxo-4-chlorobutyl)-3,4-dihydrocarbostyril was mixed with 100 ml of methanol, and the mixture was stirred at a room temperature. Then 1.0 g of sodium borohydride was added to the mixture gradually. After the reaction mixture was stirred at a room temperature for 2 hours, methanol was removed by distillation under a reduced pressure. The residue was extracted with chloroform and the chloroform layer was washed with water, and dried. Chloroform was removed by distillation under a reduced pressure, then the residue thus obtained was recrystallized from ethanol-water to obtain 1.2 g of 6-(1-hydroxy-4-chlorobutyl)-3,4-dihydrocarbostyril in colorless needle-like crystals. Melting point: 120°-121° C.

Workup

  1. stirringAfter the reaction mixture was stirred at a room temperature for 2 hours
  2. custommethanol was removed by distillation under a reduced pressure
  3. extractionThe residue was extracted with chloroform
  4. washthe chloroform layer was washed with water
  5. customdried
  6. customChloroform was removed by distillation under a reduced pressure
  7. customthe residue thus obtained
  8. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-6824de05d43d4c33b3a561986ac35802
Source dataset
uspto-grants-1984_06
Patent number
US04455422

Reaction notes

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