Benzaldehyde → HCID 69176510, compound

HRID 1373888Notes

Reaction equation

HRID 1373888 reaction equation
Cl.[CH2:2]([C:6]1[N:7]([NH2:19])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:3][CH2:4][CH3:5].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(C)C>[CH:20](=[N:19][N:7]1[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=[C:6]1[CH2:2][CH2:3][CH2:4][CH3:5])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 21075714HCID 21075714, compound

Product 1

HCID 69176510HCID 69176510, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-butyl-1H-imidazo[4,5-c]quinolin-1-amine hydrochloride (503 mg, 1.82 mmol) in 10 mL of isopropanol was treated with benzaldehyde (220 μL, 2.17 mmol) and 200 mg of DOWEX W50-X1 acid resin. The reaction mixture was heated to reflux overnight. The reaction mixture was filtered, and the filtrate was treated with 0.5 mL of triethylamine and concentrated under reduced pressure. The resulting oil was dissolved in 75 mL of CH2Cl2 and washed with saturated NaHCO3 solution, H2O and brine. The organic was dried over Na2SO4, filtered and concentrated to give N-benzylidene(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (575 mg) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate was treated with 0.5 mL of triethylamine
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting oil was dissolved in 75 mL of CH2Cl2
  7. washwashed with saturated NaHCO3 solution, H2O and brine
  8. dry with materialThe organic was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-84b2e9986ca64ac09fe41e4d1db7ec0c
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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