Furfural → HCID 69177440, compound

HRID 1373913Notes

Reaction equation

HRID 1373913 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].[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH:24]=O>C(O)(C)C.Cl.C(Cl)(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[CH:24][C:20]2[O:19][CH:23]=[CH:22][CH:21]=2)[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

6

Reactant 2

HCID 7362FurfuralHCID 21075716HCID 21075716, compound

Product 1

HCID 69177440HCID 69177440, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (1.50 g, 6.19 mmol) in 20 mL of isopropanol was treated with 2-furaldehyde (1.08 mL, 13.0 mmol) and 2 drops of concentrated HCl and heated to reflux under an atmosphere of nitrogen. After 48 h, the reaction was concentrated under reduced pressure to yield a brown oil. The oil was dissolved in 30 mL of CHCl3 and washed with 5% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(furan-2-ylmethylene)amine (1.86 g) as a light brown solid.

Workup

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. concentrationthe reaction was concentrated under reduced pressure
  4. customto yield a brown oil
  5. washwashed with 5% Na2CO3 solution, water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c1cba1d3dd34009819db39f205346d6
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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