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

HRID 1626135Notes

Reaction equation

HRID 1626135 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>>[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

3

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%

Conditions

Temperature
23 °C

Procedure

To a solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (555 mg, 3.19 mmol) in dimethylsuloxide (15 ml) at 23° C. was added triethylamine (1.93 g, 2.66 ml, 19.1 mmol) and sulfur trioxide-pyridin 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 sodium sulphate, 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, 52% 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 sodium sulphate
  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-f05db2ba4e57487199a385c6c15b1ca0
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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