Triethylamine → 5,6,7,8-Tetrahydro-8-oxo-3-quinolinecarbonitrile

HRID 403251Notes

Reaction equation

HRID 403251 reaction equation
[OH:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([C:12]#[N:13])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C>CS(C)=O>[O:1]=[C:2]1[C:11]2[N:10]=[CH:9][C:8]([C:12]#[N:13])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 682271448-Hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile

Product 1

HCID 682272435,6,7,8-Tetrahydro-8-oxo-3-quinolinecarbonitrileYield 52.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (555 mg, 3.19 mmol) in DMSO (15 ml) at 23° C. was added triethylamine (1.93 g, 2.66 ml, 19.1 mmol) and sulphur trioxide-pyridine complex (1.52 g, 9.56 mmol). The brown solution was stirred at 23° C. for 2 hours. The reaction mixture was poured on water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give of a light brown solid, which was purified by silica gel flash chromatography with dichloromethane/methanol to give the 8-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile (286 mg, 1.66 mmol, 52.1% yield) as a light yellow solid. MS (ISP): m/z=173.1 [(M+H)+].

Workup

  1. additionThe reaction mixture was poured on water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give of a light brown solid, which
  8. customwas purified by silica gel flash chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-c0db23549e374b518437c7bea204d012
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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