Sodium borohydride → HCID 69202897, compound

HRID 1373901Notes

Reaction equation

HRID 1373901 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][O: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][O:23][CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69191480HCID 69191480, compound

Product 1

HCID 69202897HCID 69202897, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-benzylidene-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.00 g, 3.03 mmol) in 50 mL of MeOH was treated with NaBH4 (458 mg, 12.1 mmol). After stirring for 1.5 h, the reaction mixture was concentrated, then treated with saturated NaHCO3 solution, and extracted into CHCl3. The organic portion was washed with H2O and brine and dried over Na2SO4. The resulting solution was filtered and concentrated to give N-benzyl-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.01 g) as a tan solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiontreated with saturated NaHCO3 solution
  3. extractionextracted into CHCl3
  4. washThe organic portion was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe resulting solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eb4ec9fe5d84423da5a85eb7a6a52bef
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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