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

HRID 1467187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467187
[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-b0e0141a070a4e749cb3903d001275e6
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000054B2

Notizen zur Reaktion

Wird geladen…