Aniline → (2-Nitropyridin-3-yl)phenylamine

HRID 242970

Reaktionsgleichung

Reaktionsgleichung von HRID 242970
F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>CN(C=O)C>[N+:8]([C:3]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 8471TriethylamineHCID 27628023-Fluoro-2-nitropyridine

Produkt 1

HCID 20184004(2-Nitropyridin-3-yl)phenylamineAusbeute 154,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-fluoro-2-nitropyridine (1.07 g, 6.75 mmol), aniline (1.8 mL, 20.2 mmol) and Et3N (2.8 mL, 20.2 mmol) in DMF (10 mL) was stirred at 100° C. for 16 h under a nitrogen atmosphere. After cooling to RT, the volatiles were removed under reduced pressure. The resulting residue was partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM) to afford the title compound as a red oil (2.24 g, quantitative). LCMS (Method C): RT 3.03 min [M+H]+ 216.2.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed under reduced pressure
  3. customThe resulting residue was partitioned between DCM and water
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. dry with materialthe combined organic fractions dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8f761dc54c3a4619aa346344671b6aeb
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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