Water → 2-Butylsulfanyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile

HRID 1817812Notes

Reaction equation

HRID 1817812 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][C:10]2[NH:9][C:8](=[S:12])[C:7]([C:13]#[N:14])=[CH:6][C:5]=2[C:4](=[O:15])[CH2:3]1.[OH-].[K+].Br[CH2:20][CH2:21][CH2:22][CH3:23].O>CN(C=O)C>[CH2:20]([S:12][C:8]1[C:7]([C:13]#[N:14])=[CH:6][C:5]2[C:4](=[O:15])[CH2:3][C:2]([CH3:16])([CH3:1])[CH2:11][C:10]=2[N:9]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 19346807,7-Dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

Product 1

HCID 578832862-Butylsulfanyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrileYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7,7-dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (0.5 g, 2.2 mmol) in DMF (4 ml) was added 10% aqueous potassium hydroxide (1.23 ml), followed by dropwise addition of 1-bromobutane (0.24 ml, 2.2 mmol). The mixture was stirred at room temperature for 12 h, then water (12 ml) was added. The product was extracted with diethyl ether. The extract was washed with water and dried over sodium sulfate. Filtration and concentration under reduced pressure afforded the residue which was purified by flash chromatography on silica gel (petroleum ether-ethyl acetate, 10:1) to give the title compound (0.41 g, 59%) as a colorless solid.

Workup

  1. extractionThe product was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration under reduced pressure
  5. customafforded the residue which
  6. customwas purified by flash chromatography on silica gel (petroleum ether-ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-7cb1d760ccbb4c598d5004bcdd484af9
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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