Ethyl 2-bromopropionate → HCID 69726085, compound

HRID 1075665Notes

Reaction equation

HRID 1075665 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:41]([O:43][C:44](=[O:48])[CH:45](Br)[CH3:46])[CH3:42]>C1COCC1.ClCCl>[CH2:41]([O:43][C:44](=[O:48])[CH:45]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:46])[CH3:42]

Participants

6

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 2724141Tetrabutylammonium FluorideHCID 70213354HCID 70213354, compound

Product 1

HCID 69726085HCID 69726085, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-hydroxyquinoline-5-carbaldehyde (346 mg, 2 mmol), 2-oxindole (266 mg, 2 mmol) and piperidine (43 mg, 0.5 mmol) in absolute ethanol (10 ml) was heated for 3 h at 60-70° C. under nitrogen. Then the reaction mixture was chilled and evaporated under vacuum to dryness. The residue was submitted to column chromatography over silica gel using dichloromethane/ethanol 4% as eluant to give pure 3-(8-hydroxy-5-quinolylmethylen)-2-oxindole in 60% yield (365 mg). To a solution of 3-(8-hydroxy-5-quinolylmethylen)-2-oxindole (300 mg, 0.99 mmol) in THF (5 ml) was added at room temperature a solution of 1M tetrabutylammonium fluoride (5 ml) and 2-bromopropionic acid ethylester (0.9 ml, 6.9 mmol). The reaction mixture was stirred at room temperature for another 1 h and then diluted with dichloromethane. The organic layer was washed with 5% NaHCO3 solution and water, dried over sodium sulfate and then evaporated under vacuum. The oily residue was chromatographed on silica gel using ethyl acetate as eluant to give pure title compound in 86% yield (330 mg).

Workup

  1. washThe organic layer was washed with 5% NaHCO3 solution and water
  2. dry with materialdried over sodium sulfate
  3. customevaporated under vacuum
  4. customThe oily residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-179fd7402dbe4c08b7d847633467cdb2
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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