Ammonium Chloride → 2-Methyl-6-(methylsulfonyl)pyridin-3-amine

HRID 1811598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811598
[Cl-].[NH4+].[CH3:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])[N:5]=1>C(OCC)(=O)C.[Zn]>[CH3:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])[N:5]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 124082046-Methanesulfonyl-2-methyl-3-nitropyridine

Produkt 1

HCID 510505272-Methyl-6-(methylsulfonyl)pyridin-3-amineAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of zinc dust (146 g, 2.01 mol) and aqueous ammonium chloride solution (3 M, 800 ml) was added dropwise a solution of 2-methyl-6-(methylsulfonyl)-3-nitropyridine (87.0 g, 401 mmol) in ethyl acetate (500 mL) via an addition funnel at 0° C. The mixture was stirred at room temperature for 17 h and filtered through Celite™. The filtrate was then extracted with ethyl acetate. The organic phase was separated, dried over MgSO4, filtered, and concentrated. The residue was recrystallized from ethanol to give the title compound (34.7 g, 46%) as a solid. Exact mass calculated for C7H10N2O2S: 186.1. Found: LCMS m/z=187.2 (M+H+).

Aufarbeitung

  1. filtrationfiltered through Celite™
  2. extractionThe filtrate was then extracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d43c28ee7a2045518a3645926f4aecae
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362248B2

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