N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine → N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine

HRID 2272703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272703
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[F:18]>[Ni].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[F:18]

Komponenten

4

Edukt 1

HCID 86730067N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine

Produkt 1

HCID 61466916N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine (C11) (5.0 g, 19 mmol) and Raney nickel (3 g) in ethyl acetate (400 mL) was degassed three times with hydrogen. The reaction mixture was then hydrogenated at room temperature for 20 hours. After removal of the catalyst via filtration, the filtrate was concentrated in vacuo. Purification via silica gel chromatography afforded the product as a gray solid. Yield: 3.1 g, 13 mmol, 68%. 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, J=4.9, 1.6 Hz, 1H), 7.38 (dd, J=11.5, 2.5 Hz, 1H), 7.24 (dd, J=8.5, 8.4 Hz, 1H), 7.06 (dd, J=7.6, 1.6 Hz, 1H), 6.92 (ddd, J=8.7, 2.5, 1.0 Hz, 1H), 6.82 (dd, J=7.6, 4.9 Hz, 1H), 6.37 (br s, 1H), 3.38 (br s, 2H).

Aufarbeitung

  1. customwas degassed three times with hydrogen
  2. customAfter removal of the catalyst
  3. filtrationvia filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5aefc373734747c0880bfe4fe039bffc
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120788B2

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