Benzaldehyde → HCID 15224426, compound

HRID 396968Notes

Reaction equation

HRID 396968 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 mol) was dissolved in tetrahydrofuran (50 mL) then cooled to −78° C. A 7.75 mL portion of n-butyl lithium (2.5 M in hexanes) was added dropwise to the cooled solution. At 15 minutes post addition, benzaldehyde (2.7 mL; 0.027 mol) 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 a white crystalline solid, m.p. 160-166C. Analysis: Calculated: 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
  11. customto provide a white crystalline solid, m.p. 160-166C

Sources & evidence

ORD record
ord-d99b74db11194d4594955a83ec5e15d0
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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