2-Chloro-3-methyl-5-nitropyridine → 6-Chloro-5-methylpyridin-3-amine

HRID 367065

Reaktionsgleichung

Reaktionsgleichung von HRID 367065
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>O.CC(O)=O.[Fe]>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Komponenten

4

Edukt 1

HCID 896482-Chloro-3-methyl-5-nitropyridine

Produkt 1

HCID 122956076-Chloro-5-methylpyridin-3-amineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

2-Chloro-3-methyl-5-nitropyridine (3.2 g, 18.5 mmol; Maybridge Chemical Co.) was dissolved in a mechanically stirred solution of H2O/HOAc (60 mL, 5:1). Iron powder was added over a 5 h period, maintaining the temperature below 40° C., and stirring was continued until starting material had be consumed. The reaction mixture was filtered, and the filter cake was washed with EtOAc. The aqueous filtrate was extracted with EtOAc, and the combined organic fractions were washed with saturated NaHCO3 solution, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford 5-amino-2-chloro-3-methylpyridine as an orange solid (2.34 g, 89%): MS (CI/NH3) m/z: 143 (M+H)+ ; NMR (DMSO-d6, 300 MHz) δ 2.17 (s, 3H), 5.40 (br s, 2H), 6.90 (d, J=2.2 Hz, 1H), 7.54 (d, J=2.2 Hz, 1H).

Aufarbeitung

  1. temperaturemaintaining the temperature below 40° C.
  2. customhad be consumed
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was washed with EtOAc
  5. extractionThe aqueous filtrate was extracted with EtOAc
  6. washthe combined organic fractions were washed with saturated NaHCO3 solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-08df4e70870c43d5bdb28521a8e5eee0
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133253

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