Réaction #558741

Équation de réaction

2,6-dinitrobenzonitrile

isopropylamine

→

2-(isopropylamino)-6-nitrobenzonitrile

Rendement 35.7%

Solvants

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source