N-cyclopropyl-4,5-difluoro-2-nitroaniline → N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

HRID 1048953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048953
[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=2[N+:13]([O-])=O)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([NH:4][C:5]2[C:6]([NH2:13])=[CH:7][C:8]([F:12])=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 86703086N-cyclopropyl-4,5-difluoro-2-nitroaniline

Produkt 1

HCID 68053726N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To the title compound from Step A (1.22 g, 5.69 mmol) were added 10% palladium on carbon (0.122 g, 1.15 mmol) and methanol (28.5 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was then filtered through CELITE® using dichloromethane, and the filtrate was concentrated. Purification by flash chromatography on silica gel (0-30% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.83 (dd, J=12.4, 7.9 Hz, 1 H), 6.51 (dd, J=11.3, 7.8 Hz, 1 H), 3.82 (br s, 1 H), 3.15 (br s, 2 H), 2.40-2.37 (m, 1 H), 0.77-0.73 (m, 2 H), 0.52-0.50 (m, 2 H).

Aufarbeitung

  1. filtrationThe mixture was then filtered through CELITE®
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography on silica gel (0-30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d9f95678cdfc4c0f9b7b20912fcc376d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382226B2

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