Ammonium Chloride → 2-methyl-6-(1H-1,2,4-triazol-1-yl)pyridin-3-amine

HRID 1931573

Reaktionsgleichung

Reaktionsgleichung von HRID 1931573
[Cl-].[NH4+].[CH3:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[N:5]=1>C(OCC)(=O)C.[Zn]>[CH3:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[N:5]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 579651682-Methyl-3-nitro-6-(1H-1,2,4-triazol-1-yl)pyridine

Produkt 1

HCID 532992722-methyl-6-(1H-1,2,4-triazol-1-yl)pyridin-3-amineAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of zinc (Aldrich, <10 micron; 798 mg, 12.2 mmol) in aqueous ammonium chloride (2 M; 6.1 mL, 12.2 mmol) was cooled to 0° C. using an ice-water bath, and stirred at this temperature for 15 min. A solution of 2-methyl-3-nitro-6-[1,2,4]triazol-1-yl-pyridine (500 mg, 2.44 mmol) in ethyl acetate (8 mL) was added and the mixture was stirred at 0° C. for 1 h and then at room temperature overnight. The mixture was then filtered through Celite™ to remove zinc dust, and the Celite™ was washed with ethyl acetate and methanol. Water and ethyl acetate were added to the filtrate and the mixture was shaken and then filtered to remove some solid material between the two layers. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were evaporated to dryness under high vacuum to give 2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-ylamine (322 mg, 75%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H), 5.37 (s, 2H), 7.11 (d, 1H, J=8.4 Hz), 7.38 (d, 1H, J=8.4 Hz), 8.13 (s, 1H), 9.03 (s, 1H).

Aufarbeitung

  1. stirringthe mixture was stirred at 0° C. for 1 h
  2. customat room temperature
  3. customovernight
  4. filtrationThe mixture was then filtered through Celite™
  5. customto remove zinc dust
  6. washthe Celite™ was washed with ethyl acetate and methanol
  7. additionWater and ethyl acetate were added to the filtrate
  8. stirringthe mixture was shaken
  9. filtrationfiltered
  10. customto remove some solid material between the two layers
  11. extractionThe aqueous layer was extracted twice with ethyl acetate
  12. customthe combined organic layers were evaporated to dryness under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ea458cd4434d4d14b4e836102b8328cd
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188098B2

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