Chloroform → HCID 21075786, compound

HRID 1373916Notes

Reaction equation

HRID 1373916 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[C:19]([CH2:22][CH3:23])[CH2:20][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][CH:19]([CH2:20][CH3:21])[CH2:22][CH3:23])[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 21075787HCID 21075787, compound

Product 1

HCID 21075786HCID 21075786, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(1-ethylpropylidene)amine (1.78 g, 5.73 mmol) in 20 mL of methanol was treated with NaBH4 (0.867 g, 22.9 mmol) and CeCl3.7H2O (15 mg, catalytic) and stirred under an atmosphere of nitrogen. After 24 h, the reaction was concentrated under reduced pressure, dissolved CHCl3, washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a yellow/green syrup. Chromatography (SiO2, 93:7 CHCl3:MeOH) gave N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(1-ethylpropyl)amine (1.01 g) as a yellow/green oil.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. dissolutiondissolved CHCl3
  3. washwashed with water (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a yellow/green syrup

Sources & evidence

ORD record
ord-698be7abaed14e8db2f83987982542bc
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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