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

HRID 711696Notes

Reaction equation

HRID 711696 reaction equation
[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]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 520718Dinitrobenzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2c6e811ffa4b459380b96ad667b19017
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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