Sodium borohydride → HCID 21075809, compound

HRID 1373939Notes

Reaction equation

HRID 1373939 reaction equation
[C:1](=[N:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21075812HCID 21075812, compound

Product 1

HCID 21075809HCID 21075809, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-isopropylidene-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (4.30 g, 16.1 mmol) in 100 mL of methanol was cooled in an ice water bath. The solution was treated with sodium borohydride (3.05 g, 80.7 mmol) over 5 min. The reaction mixture was allowed to warm to ambient temperature. After 2.5, the reaction was quenched by addition of 15 mL of saturated NH4Cl solution. The mixture was concentrated under reduced pressure to yield a light brown solid. The solid was partitioned between 100 mL CHCl3 and 25 mL of saturated NaHCO3 solution and then separated. The organic portion was washed with water (25 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown solid. The solid was purified by chromatography (SiO2, 97:2.5:0.5 CHCl3:MeOH:NH4OH) to give 2.48 g of N-isopropyl-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine as a tan solid.

Workup

  1. customAfter 2.5, the reaction was quenched by addition of 15 mL of saturated NH4Cl solution
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto yield a light brown solid
  4. customThe solid was partitioned between 100 mL CHCl3 and 25 mL of saturated NaHCO3 solution
  5. customseparated
  6. washThe organic portion was washed with water (25 mL), brine (25 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a light brown solid
  11. customThe solid was purified by chromatography (SiO2, 97:2.5:0.5 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-ea4a2413c2e44958a0e920b73d149ccf
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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