(2-Nitropyridin-3-yl)phenylamine → N3-Phenylpyridine-2,3-diamine

HRID 242971

Reaktionsgleichung

Reaktionsgleichung von HRID 242971
[N+:1]([C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O>CCOC(C)=O>[C:11]1([NH:10][C:9]2[C:4]([NH2:1])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

3

Edukt 1

HCID 20184004(2-Nitropyridin-3-yl)phenylamine

Produkt 1

HCID 68018423N3-Phenylpyridine-2,3-diamineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (2-nitropyridin-3-yl)phenylamine (6.75 mmol) in EtOAc (40 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (200 mg) and was stirred at RT under a hydrogen atmosphere for 16 h. The suspension was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a white solid (520 mg, 42% over two steps). 1H NMR (CDCl3, 400 MHz): δ 7.92 (1H, dd, J=4.98, 1.64 Hz), 7.36 (1H, ddd, J=7.62, 1.65, 0.69 Hz), 7.26-7.20 (2H, m), 6.90-6.85 (1H, m), 6.78-6.73 (2H, m), 6.68 (1H, dd, J=7.61, 4.98 Hz), 5.13 (1H, br s), 4.57 (2H, br s).

Aufarbeitung

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (200 mg)
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-2c60a90b4c7e4e1495645e1894d7e3a9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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