Imidazole → HCID 22448927, compound

HRID 2186737Notes

Reaction equation

HRID 2186737 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].O>CN(C=O)C>[O:1]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)[Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 135441757Quinolin-5-ol

Product 1

HCID 22448927HCID 22448927, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-hydroxyquinoline (101 mg) was dissolved in DMF (5 ml) under an argon atmosphere, and the resultant solution was stirred at room temperature. Imidazole (113 mg) and t-butyldimethylsilyl chloride (162 mg) were added to the solution, and the mixture was stirred at room temperature. After disappearance of the raw materials was confirmed, water (5 ml) was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=9/1) to obtain the object compound (197 mg, yield 100%).

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-4a0550ec2dba45a7ade37b81d421a669
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

Loading…