3-(Trifluoromethyl)aniline → 2-Methyl-7-(trifluoromethyl)quinoline

HRID 338858

反応式

HRID 338858 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH:12](=O)/[CH:13]=[CH:14]/[CH3:15].C(OCC)(=O)C>Cl.O>[CH3:15][C:14]1[CH:13]=[CH:12][C:7]2[C:5](=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:9][CH:8]=2)[N:6]=1

参加物

6

反応物 3

HCID 73753-(Trifluoromethyl)anilineHCID 8857Ethyl AcetateHCID 447466Crotonaldehyde

生成物 1

HCID 224169042-Methyl-7-(trifluoromethyl)quinoline収率 28.9%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

実験手順

To a solution of 3-(trifluoromethyl)aniline (12.43 mL, 99.92 mmol) in 6 N HCl (50 mL) in water was added (E)-but-2-enal (18.77 mL, 229.8 mmol) dropwise at reflux. The reaction was stirred at reflux for 3 hours. After cooling to ambient temperature, ethyl acetate (200 mL) was added. The aqueous layer was separated, basified with ammonium hydroxide to about pH 9, and extracted with DCM (2×200 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 2-methyl-7-(trifluoromethyl)quinoline (6.1 g, 28.9%) as a solid.

後処理

  1. temperatureat reflux
  2. temperatureat reflux for 3 hours
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (2×200 mL)
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-f0ad4393e48c40d8b061304cc8e6b1e3
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

関連ノート

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