Sodium Sulfate → 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline

HRID 2192210Notes

Reaction equation

HRID 2192210 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=O)[CH2:9]1.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][C:8]1([CH3:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-oneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of LiAlH4 (1.0 M in THF, 35 mL, 35 mmol), was added a solution of 1a. (2.17 g, 12.4 mmol) in THF (10 mL) for 5 min at 0° C. under nitrogen. The resulting mixture was warmed gradually to reflux, and heated at reflux for 5.5 h. To the cooled mixture with stirring, was added sat'd Na2SO4 dropwise till the complete decomposition of LiAlH4. The mixture was filtered, and rinsed with EtOAc. The organic was washed with H2O, brine, dried (MgSO4), and concentrated to dryness. It was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes) to give pure 1b (1.86 g, yield: 93%). LC-MS ESI 162 (M+H).

Workup

  1. temperatureThe resulting mixture was warmed gradually
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureat reflux for 5.5 h
  5. filtrationThe mixture was filtered
  6. washrinsed with EtOAc
  7. washThe organic was washed with H2O, brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated to dryness
  10. customIt was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c8a5673232884f70810f8d465b6aa49a
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

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