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

HRID 711696노트

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HRID 711696 반응식
[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]

참가 물질

4

반응물 2

HCID 6363IsopropylamineHCID 520718Dinitrobenzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2c6e811ffa4b459380b96ad667b19017
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181276B2

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