Potassium Carbonate → N-cyclopropyl-4,5-difluoro-2-nitroaniline

HRID 1048952노트

반응식

HRID 1048952 반응식
F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH:21]1([NH2:24])[CH2:23][CH2:22]1>ClCCl>[CH:21]1([NH:24][C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:23][CH2:22]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 522689Potassium Fluoride

생성물 1

HCID 86703086N-cyclopropyl-4,5-difluoro-2-nitroaniline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

2,4,5-Trifluoronitrobenzene (2.00 g, 11.3 mmol), potassium fluoride (0.656 g, 11.3 mmol), potassium carbonate (1.561 g, 11.29 mmol), and cyclopropylamine (0.93 ml, 13.55 mmol) were added to a vial and heated in a microwave at 90° C. for 10 min. The reaction was then diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 8.04 (dd, J=10.4, 8.5 Hz, 1 H), 7.09 (dd, J=12.6, 7.0 Hz, 1 H), 2.55-2.54 (m, 1 H), 0.97-0.93 (m, 2 H), 0.69-0.66 (m, 2 H).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-e38663c16df94e1e8524b7f57fc221d4
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382226B2

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