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

HRID 1763267

Reaction equation

[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

Participants

Conditions

Temperature: 260 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-28f60f3fd5ca4fb899d4b52195d8ecc3
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04111944

Linked notes

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