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

HRID 711696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711696
[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]

Komponenten

4

Edukt 2

HCID 6363IsopropylamineHCID 520718Dinitrobenzonitrile

Produkt 1

HCID 574159382-Nitro-6-[(propan-2-yl)amino]benzonitrileAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2c6e811ffa4b459380b96ad667b19017
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181276B2

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