Isopropylamine → 5-Fluoro-N-isopropyl-2-nitroaniline

HRID 243121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243121
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC[N:14](C(C)C)[CH:15]([CH3:17])[CH3:16].C(N)(C)C>C(#N)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:14][CH:15]([CH3:17])[CH3:16])[CH:7]=1

Komponenten

5

Edukt 3

HCID 6363IsopropylamineHCID 679672,4-DifluoronitrobenzeneHCID 81531Diisopropylethylamine

Produkt 1

HCID 106318075-Fluoro-N-isopropyl-2-nitroanilineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2,4-Difluoro-1-nitrobenzene (2.00 g, 12.57 mmol) was dissolved in acetonitrile (20 mL) and DIPEA (2.2 mL, 12.57 mmol) added, followed by isopropylamine (1.07 mL, 12.57 mmol). The bright yellow mixture was stirred at RT overnight. The resultant mixture was concentrated in vacuo and the residue purified by column chromatography (silica gel, gradient 0-5% EtOAc in cyclohexane) to afford the title compound as a yellow gum (2.1 g, 99%). Contaminated with some unreacted 2,4-difluoro-1-nitrobenzene, but used in the next step without any further purification. 1H NMR (CDCl3, 400 MHz): δ 8.20 (1H, dd, J=9.53, 6.21 Hz), 6.48 (1H, dd, J=11.71, 2.63 Hz), 6.33 (1H, m), 3.80-3.64 (1H, m), 1.33 (6H, d, J=6.36 Hz)

Aufarbeitung

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customthe residue purified by column chromatography (silica gel, gradient 0-5% EtOAc in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-6f72fbf8b8554a299f2dc59a372b8a85
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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