Isopropylamine → 2-Nitro-6-[(propan-2-yl)amino]benzonitrile

HRID 471559ノート

反応式

HRID 471559 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[CH:15](N)([CH3:17])[CH3:16]>CN(C=O)C>[CH:15]([NH:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([CH3:17])[CH3:16]

参加物

4

反応物 2

HCID 6363IsopropylamineHCID 520718Dinitrobenzonitrile

生成物 1

HCID 574159382-Nitro-6-[(propan-2-yl)amino]benzonitrile収率 35.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2,6-dinitrobenzonitrile (0.58 g, 3.00 mmol) in DMF (6 mL) was added isopropylamine (0.71 g, 12.00 mmol) and the reaction mixture was stirred at 50° C. under nitrogen for ten minutes. After cooling to room temperature, dilution with H2O and extraction with EtOAc, solvents of the combined organic phases were evaporated and the residue was purified by flash chromatography (Biotage system, 80 g silicagel column) using a Hexane/EtOAc (3:2) solution as eluant, to give 2-(isopropylamino)-6-nitrobenzonitrile (0.22 g, 35%). 1H NMR (400 MHz, DMSO-d6) δ 1.20 (d, J=6.4 Hz, 6H), 3.85-3.80 (m, 1H), 5.94 (d, J=8.0 Hz, NH), 7.26 (d, J=9.0 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 7.60 (t, J=8.8 Hz, 1H).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractiondilution with H2O and extraction with EtOAc, solvents of the combined organic phases
  3. customwere evaporated
  4. customthe residue was purified by flash chromatography (Biotage system, 80 g silicagel column)

出典と根拠

ORDレコード
ord-7d43877c3ba2491f9309c626b8cbe3c0
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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