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

HRID 748208Notes

Reaction equation

HRID 748208 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-310055cb1f2748cd8b496ec84e4cf7e8
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…