3-Methylbutanal → HCID 69176562, compound

HRID 1373922Notes

Reaction equation

HRID 1373922 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].[CH:19](=O)[CH2:20][CH:21]([CH3:23])[CH3:22]>C1(C)C=CC=CC=1.C(O)(C)C.C(Cl)(Cl)Cl.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]=[CH:19][CH2:20][CH:21]([CH3:23])[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

7

Reactant 2

HCID 115523-MethylbutanalHCID 21075716HCID 21075716, compound

Product 1

HCID 69176562HCID 69176562, compoundYield 99.8%

Reagents, catalysts & solvents 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (1.00 g, 4.13 mmol) in 20 mL of toluene and 5 mL of isopropanol was treated with isovaleraldehyde (0.94 mL, 8.76 mmol) and pyridinium p-toluenesulfonate (0.052 g, 0.21 mmol) and the reaction mixture was heated to reflux under an atmosphere of nitrogen. After 15 h, the reaction mixture was concentrated under reduced pressure to yield a brown oil. The oil was dissolved in CHCl3 and washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(3-methylbutylidene)amine (1.28 g) as a dark orange oil.

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. customto yield a brown oil
  5. washwashed with water (2×) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55d08a3ea83648468c37665663ac11fb
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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