Imidazole → 8-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

HRID 1095672Notes

Reaction equation

HRID 1095672 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[Si:23]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5993428-Hydroxy-2-quinolinecarboxaldehyde

Product 1

HCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehydeYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

8-Hydroxyquinoline-2-carbaldehyde (5.00 g, 28.9 mmol) and imidazole (4.32 g, 63.5 mmol) was dissolved in dichloromethane (50 mL) under an atmosphere of dry N2. The reaction mixture was then cooled to 0° C. and tert-butylchlorodimethylsilane (4.94 g, 31.8 mmol) was added. The reaction was stirred overnight at ambient temperature, and then partitioned between dichloromethane and water. The organic layer was washed with water and aqueous saturated NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification via flash chromatography (2:1 Hexanes/dichloromethane followed by 1:1 hexanes/dichloromethane) provided 6.50 g, 78% of the desired product as an oil.

Workup

  1. custompartitioned between dichloromethane and water
  2. washThe organic layer was washed with water and aqueous saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification via flash chromatography (2:1 Hexanes/dichloromethane followed by 1:1 hexanes/dichloromethane)

Sources & evidence

ORD record
ord-0039320c4edc444d8a04c3ba97a7e372
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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