Sodium Hydroxide → 3-Butyryl-4-(2-methylphenylamino)-8oxiranylquinoline

HRID 1090663Notes

Reaction equation

HRID 1090663 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]=[O:25])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:26]OS([O-])(=O)=O.C[S+](C)C.[OH-].[Na+]>ClCCl.O>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]1[CH2:26][O:25]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 2760871Trimethylsulfonium methyl sulfate2×HCID 103821023-Butyryl-4-(o-tolylamino)quinoline-8-carbaldehyde

Product 1

HCID 99749123-Butyryl-4-(2-methylphenylamino)-8oxiranylquinolineYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)quinoline-8-carbaldehyde (0.5 q, 1.5 mmol) was dissolved in dichloromethane (5 ml) and trimethylsulphonium methylsulphate (0.34 g, 1.8 mmol) and 50% aqueous sodium hydroxide (0.75 ml) added. The mixture was stirred vigorously for 2.5 hours, when a further addition of trimethylsulphonium methylsulphate (0.23 g, 1.2 mmol) and 50% aqueous sodium hydroxide (0.5 ml) was made. After stirring for a further 2 hours the mixture was diluted with water and extracted with dichloromethane. The dried extracts were evaporated to an oil, which was purified by flash chromatography (silica gel, ethyl acetate/chloroform). The product crystallised on trituration with petroleum ether to give 3-butyryl-4-(2-methylphenylamino)-8-oxiranylquinoline (0.28 g, 54%), m.p. 114°-116°.

Workup

  1. stirringAfter stirring for a further 2 hours the mixture
  2. extractionextracted with dichloromethane
  3. customThe dried extracts were evaporated to an oil, which
  4. customwas purified by flash chromatography (silica gel, ethyl acetate/chloroform)
  5. customThe product crystallised on trituration with petroleum ether

Sources & evidence

ORD record
ord-9663e03627d94ea28dd95ea2b0afbe54
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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