Sodium borohydride → HCID 21075781, compound

HRID 1373945Notes

Reaction equation

HRID 1373945 reaction equation
[N:1]1([N:14]=[C:15]([CH3:17])[CH3:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[BH4-].[Na+]>CO>[N:1]1([NH:14][CH:15]([CH3:17])[CH3:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21075782HCID 21075782, compound

Product 1

HCID 21075781HCID 21075781, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine (3.48 g, 15.5 mmol) in 75 mL of methanol was cooled in an ice water bath. The solution was treated over 5 min with sodium borohydride (2.94 g, 77.6 mmol). After 1 h, the reaction mixture was quenched with 20 mL of saturated NH4Cl solution and then concentrated under reduced pressure to yield a brown soild. The solid was partitioned between 80 mL CHCl3 and 20 mL saturated NaHCO3 solution and the phases were separated. The organic portion was washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown solid. The solid was purified by chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) to give 1.28 g of N-(1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine as a tan foam.

Workup

  1. customthe reaction mixture was quenched with 20 mL of saturated NH4Cl solution
  2. concentrationconcentrated under reduced pressure
  3. customto yield a brown soild
  4. customThe solid was partitioned between 80 mL CHCl3 and 20 mL saturated NaHCO3 solution
  5. customthe phases were separated
  6. washThe organic portion was washed with water (20 mL), brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a brown solid
  11. customThe solid was purified by chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-dda939bbd8294ca7b624d2520b9f5a64
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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