Chloroform → HCID 21075792, compound

HRID 1373919Notes

Reaction equation

HRID 1373919 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[CH:19][CH:20]([CH3:22])[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)[CH3:2].[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH:20]([CH3:21])[CH3:22])[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)[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 69176012HCID 69176012, compound

Product 1

HCID 21075792HCID 21075792, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isobutylideneamine (1.15 g, 3.88 mmol) in 15 mL of methanol was treated with NaBH4 (0.44 g, 11.6 mmol) and stirred under an atmosphere of nitrogen. After 18 h, the reaction was concentrated under reduced pressure. The residue was partitioned between CHCl3 and water, and the phases were separated. The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield an orange oil. Chromatography (SiO2, 97:3 CHCl3:MeOH), gave N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isobutylamine (0.69 g) as clear, colorless crystals.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customThe residue was partitioned between CHCl3 and water
  3. customthe phases were separated
  4. washThe organic portion was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield an orange oil

Sources & evidence

ORD record
ord-0a7dab81ee4344d2b026fd5fdf9b713e
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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