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

HRID 1048952ノート

反応式

HRID 1048952 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e38663c16df94e1e8524b7f57fc221d4
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

反応ノート

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