Stannous chloride dihydrate → 2-(2-Methoxyphenyl)-3-pyridinamine

HRID 1431442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431442
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 59631504HCID 59631504, Verbindung

Produkt 1

HCID 116441022-(2-Methoxyphenyl)-3-pyridinamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a stirred mixture of 2-(2-methoxyphenyl)-3-nitropyridine (34.3 mg, 0.15 mmol) in EtOAc (5.0 mL) was added tin(II) chloride dihydrate (0.17 g, 0.76 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 65° C. After 19 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH (10 mL), water (10 mL), and brine (10 mL). After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was identified as mostly 2-(2-Methoxyphenyl)-3-pyridinamine. Mass Spectrum (pos.) m/e: 201.1 (M+1).

Aufarbeitung

  1. additionUpon complete addition of the reducing agent
  2. temperaturethe reaction was cooled to rt
  3. washwashed with 1M NaOH (10 mL), water (10 mL), and brine (10 mL)
  4. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  5. customthe organic solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5191604c958a45af89c3b66510eae792
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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