Methanol → HCID 21075787, compound

HRID 1373915Notes

Reaction equation

HRID 1373915 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH2:18])[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].[CH3:19][CH2:20][C:21](=O)[CH2:22][CH3:23].C(Cl)(Cl)Cl.CO>C1(C)C=CC=CC=1.C(O)(C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[C:21]([CH2:22][CH3:23])[CH2:20][CH3:19])[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

8

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 7288Ethyl ketoneHCID 21075716HCID 21075716, compound

Product 1

HCID 21075787HCID 21075787, compoundYield 92.6%

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (1.50 g, 6.19 mmol) in 20 mL of toluene and 5 mL of isopropanol was treated with 3-pentanone (5.00 mL, 47.2 mmol) and pyridinium p-toluenesulfonate (0.015 g, 0.062 mmol) and the reaction mixture was heated to reflux under an atmosphere of nitrogen. After 7 d, the reaction mixture was concentrated under reduced pressure, dissolved in CHCl3, washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown oil. Chromatography (SiO2, 95:5 CHCl3:MeOH) gave N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(1-ethylpropylidene)amine (1.78 g) as a yellow/green syrup.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutiondissolved in CHCl3
  5. washwashed with water (2×) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a light brown oil

Sources & evidence

ORD record
ord-9cb0f373c5e14397ab9190e9eafc6aaf
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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