4-Cyanopyridine → 2-methyl-4-(3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)pyridine

HRID 1763267

Reaktionsgleichung

Reaktionsgleichung von HRID 1763267
[Na].[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)#[N:3].[CH3:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][N:20]=1)[C:14]([NH:16][NH2:17])=O>CO>[N:7]1[CH:8]=[CH:9][C:4]([C:2]2[NH:17][N:16]=[C:14]([C:13]3[CH:18]=[CH:19][N:20]=[C:11]([CH3:10])[CH:12]=3)[N:3]=2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 75064-CyanopyridineHCID 3225492-Methylisonicotinic acid hydrazideHCID 5360545Sodium

Produkt 1

HCID 203097492-methyl-4-(3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
260 °C

Versuchsvorschrift

Sodium (0.4 grams) is added to 4-cyanopyridine (8.3 grams, 0.08 mole) in methanol, and the solution is allowed to stand 30 minutes at room temperature. A suspension of 2-methylisonicotinic acid hydrazide (0.07 mole) in methanol (160 ml.) is added, and the resulting solution is heated at reflux for 30 minutes. After cooling, the intermediate acylamidrazone is collected by filtration. The acylic intermediate is then heated at 260° C. for 15 minutes, after which the reaction is cooled to room temperature. Upon recrystallization from acetonitrile-water, 5-(4-pyridyl)-3-(2-methyl-4-pyridyl)-1,2,4-triazole is obtained, m.p. 245°-248° C.

Aufarbeitung

  1. additionis added
  2. temperaturethe resulting solution is heated
  3. temperatureat reflux for 30 minutes
  4. temperatureAfter cooling
  5. filtrationthe intermediate acylamidrazone is collected by filtration
  6. temperatureafter which the reaction is cooled to room temperature
  7. customUpon recrystallization from acetonitrile-water

Quellen und Nachweise

ORD-Eintrag
ord-28f60f3fd5ca4fb899d4b52195d8ecc3
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04111944

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