Benzaldehyde → HCID 15224426, compound

HRID 1682118Notes

Reaction equation

HRID 1682118 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1.C([Li])CCC.[CH:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[CH3:1][CH:2]([CH3:17])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[OH:30]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 11424651DeaminoimiquimodHCID 178418339Butyllithium

Product 1

HCID 15224426HCID 15224426, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinoline (4 g; 0.017 mole) was dissolved in 50 mL of tetrahydrofuran then cooled to -78° C. A 7.75 mL portion of n-butyl lithium (2.5M in hexanes) was added dropwise to the cooled solution. At 15 minutes post addition, benzaldehyde (2.7 mL; 0.027 mole) was added and the reaction mixture was allowed to warm slightly. The reaction was quenched with water then diluted with ethyl ether. The ether was separated, dried with magnesium sulfate then concentrated under vacuum. The resulting residue was purified by silica gel chromatography using 5% methanol in methylene chloride as the eluent to give an oily yellow solid. This material was recrystallized from methylene chloride/hexane to provide 1-(2-Methylpropyl)-α-phenyl-1H-imidazo[4,5-c]quinoline-2-methanol as a white crystalline solid, m.p. 160°-166° C. Analysis: Calc'd: C, 76.1; H, 6.4; N, 12.7; Found: C, 75.9; H, 6.3; N, 12.7.

Workup

  1. additionwas added
  2. temperatureto warm slightly
  3. customThe reaction was quenched with water
  4. additionthen diluted with ethyl ether
  5. customThe ether was separated
  6. dry with materialdried with magnesium sulfate
  7. concentrationthen concentrated under vacuum
  8. customThe resulting residue was purified by silica gel chromatography
  9. customto give an oily yellow solid
  10. customThis material was recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-e6e36dc739664249ab55288b40f8d6f5
Source dataset
uspto-grants-1992_12
Patent number
US05175296

Reaction notes

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