Acetone → HCID 10491789, compound

HRID 1075672Notes

Reaction equation

HRID 1075672 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.CC(C)=O.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([O:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 7498Benzyl BromideHCID 2753638-Hydroxyquinoline-5-carbaldehyde

Product 1

HCID 10491789HCID 10491789, compoundYield 55.1%

Procedure

To a solution of 8-hydroxyquinoline-5-carbaldehyde (346 mg, 2 mmol) in acetone (15 ml) anhydrous potassium carbonate (300 mg, 2.2 mmol) and benzylbromide (0.25 ml, 360 mg, 2.1 mmol) were added at 50° C. and the stirring was-continued for other 4 h at this temperature. The solvent was removed under reduced pressure, the residue taken up with dichloromethane, the organic layer washed several times with water, dried (sodium sulfate) and evaporated under vacuum. The residue was chromatographed on silica gel using as eluant ethylacetate/cyclohexane (2:3) to give 290 mg (55% yield) of 8-benzyloxyquinoline-5-carbaldehyde. The above obtained compound (290 mg, 1.1 mmol) was dissolved in ethanol (10 ml), then 2-oxindole (170 mg, 1.28 mmol) and piperidine (0.15 ml) were added and the, mixture maintained for 4 h at about 60° C. After cooling the precipitate was filtered, washed with cold ethanol and dried to give 300 mg (72% yield) of raw 3-(8-benzyloxyquinol-5-ylmethylen)-2-oxindole.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe organic layer washed several times with water
  3. dry with materialdried (sodium sulfate)
  4. customevaporated under vacuum
  5. customThe residue was chromatographed on silica gel using as eluant ethylacetate/cyclohexane (2:3)

Sources & evidence

ORD record
ord-8fe3c570fffc4900aa69acab72edca1a
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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