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

HRID 499391ノート

反応式

HRID 499391 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 114464875,6,7,8-Tetrahydroquinoline-2-carbonitrile収率 17.2%

試薬・触媒・溶媒 1

HCID 6587Nitroethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2d8b371bf17f4466a504228477791283
出典データセット
uspto-grants-2010_08
特許番号
US07767665B2

反応ノート

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