Sodium borohydride → HCID 15053185, compound

HRID 1088820Notes

Reaction equation

HRID 1088820 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH3:22])[CH2:19][CH2:18][C:17]2=[O:23].[BH4-].[Na+]>CO>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH3:22])[CH2:19][CH2:18][CH:17]2[OH:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15053184HCID 15053184, compound

Product 1

HCID 15053185HCID 15053185, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-(2-benzimidazolyl)thiomethyl-1-methyl-4-oxo-1,2,3,4-tetrahydroquinoline (300 mg) in methanol (10 ml) was added gradually sodium borohydride (35 mg) at 0° C. The reaction mixture was stirred for 40 minutes at room temperature. After distilling off the solvent, the resulting residue was extracted with dichloromethane, washed with water, and dried. Then the solvent was distilled off and the resulting residue was recrystallized from ethyl acetate-n-hexane to give 8-(2-benzimidazolyl)thiomethyl-1-methyl-4-hydroxy-1,2,3,4-tetrahydroquinoline (238 mg).

Workup

  1. distillationAfter distilling off the solvent
  2. extractionthe resulting residue was extracted with dichloromethane
  3. washwashed with water
  4. customdried
  5. distillationThen the solvent was distilled off
  6. customthe resulting residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-bfc36c35451343469e19d103192d3d22
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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