Sodium borohydride → HCID 21075783, compound

HRID 1373886Notes

Reaction equation

HRID 1373886 reaction equation
[CH2:1]([C:5]1[N:6]([N:18]=[C:19]([CH3:21])[CH3:20])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>CO>[CH2:1]([C:5]1[N:6]([NH:18][CH:19]([CH3:20])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21075784N-(2-Butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-2-imine

Product 1

HCID 21075783HCID 21075783, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine (406 mg, 1.45 mmol) in 15 mL of MeOH was treated with NaBH4 (500 mg, 13.2 mmol). After stirring for 2 days (d), the reaction was quenched with saturated NaHCO3 solution and extracted into ethyl acetate (EtOAc). The organic portion was washed with H2O and brine and dried over Na2SO4. Chromatography (SiO2, EtOAc) gave N-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (372 mg) as a mauve solid.

Workup

  1. customthe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted into ethyl acetate (EtOAc)
  3. washThe organic portion was washed with H2O and brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-de3c1034073946dea29fd41448517309
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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