Sodium borohydride → HCID 21075801, compound

HRID 1373889Notes

Reaction equation

HRID 1373889 reaction equation
[CH:1](=[N:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69176510HCID 69176510, compound

Product 1

HCID 21075801HCID 21075801, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-benzylidene(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (575 mg, 1.75 mmol) in 40 mL of MeOH was treated with NaBH4 (250 mg, 6.58 mmol). After stirring for 4 h, the reaction was quenched with saturated NaHCO3 solution and extracted into CHCl3. The organic portion was washed with H2O and brine and dried over Na2SO4. Chromatography (SiO2, 50–67% EtOAc/hexanes) gave N-benzyl(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (427 mg) as a yellow solid.

Workup

  1. customthe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted into CHCl3
  3. washThe organic portion was washed with H2O and brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-9659a6d68317418e99acea3b4ec2c61f
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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