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

HRID 3319

Reaktionsgleichung

Reaktionsgleichung von HRID 3319
[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 (15 g, 86.9 mmol; from Maybridge Chemical Co.) was dissolved in a solution of H2O/AcOH (5:1, 60 mL). Iron powder was added to the reaction mixture while maintaining the temperature below 40° C., and the mixture was stirred for 5 hours. The mixture was filtered through celite and the aqueous filtrate was extracted with EtOAc (4×). The filter cake was washed with EtOAc, and the EtOAc solutions were combined, dried (MgSO4), concentrated and chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford an orange solid (2.3 g, 89%): 1H NMR (CD3OD, 300 MHz) δ2.25 (s, 3H), 7.01 (d, J=2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H); MS (CI/NH3) m/z: 243/245 (M+H)+.

Aufarbeitung

  1. temperaturewhile maintaining the temperature below 40° C.
  2. filtrationThe mixture was filtered through celite
  3. extractionthe aqueous filtrate was extracted with EtOAc (4×)
  4. washThe filter cake was washed with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed (silica gel; CHCl3 /MeOH, 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-fb181b43b2cf48a49bb845d00e4222a4
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733912

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