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

HRID 338858

반응식

HRID 338858 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 224169042-Methyl-7-(trifluoromethyl)quinoline수율 28.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f0ad4393e48c40d8b061304cc8e6b1e3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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