Dimethylcarbamoyl Chloride → 5,6,7,8-Tetrahydroquinoline-2-carbonitrile

HRID 499391Notes

Reaction equation

HRID 499391 reaction equation
[N+:1]1([O-])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Si]([C:16]#[N:17])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:16]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1)#[N:17]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 27781345,6,7,8-Tetrahydro-1-quinoliniumolate

Product 1

HCID 114464875,6,7,8-Tetrahydroquinoline-2-carbonitrileYield 17.2%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

5,6,7,8-Tetrahydroquinoline N-oxide (3.0 g, 19.1 mmol) was dissolved in nitroethane (30 ml), and trimethylsilyl cyanide (2.1 g, 21.0 mmol) and N,N-dimethylcarbamoyl chloride (2.1 g, 19.1 mmol) were added thereto. The reaction mixture was stirred at room temperature for 3 days, concentrated under reduced pressure, combined with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v) to give the titled compound (0.52 g, 17%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (2:1

Sources & evidence

ORD record
ord-2d8b371bf17f4466a504228477791283
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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