4-Cyanopyridine → 4-[5-(Pyridin-4-yl)-1H-1,2,4-triazol-3-yl]aniline

HRID 263126

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[Na].[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([NH:17][NH2:18])=O)=[CH:13][CH:12]=1>CO>[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]2[N:2]=[C:1]([C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)[NH:18][N:17]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 245 °C

Procedure

To 4-cyanopyridine (4.2 g.) in methanol (60 ml.) is added sodium (0.2 g.). The solution is allowed to stand for 0.5 hour at room temperature and is then added to a suspension of p-aminobenzhydrazide (6.4 g.) in 150 ml. of methanol. The resulting solution is heated 20 hours at reflux during which time a solid separates. The solid is filtered and heated to 245° C. over one hour and maintained at that temperature for an additional 15 minutes. After cooling the solid is recrystallized from a mixture of acetonitrile and water to yield 3-(p-aminophenyl)-5-(4-pyridyl)-1,2,4-triazole (2 g.) m.p. 251°-252.5° C.

Workup

temperatureThe resulting solution is heated 20 hours
temperatureat reflux during which time a solid separates
filtrationThe solid is filtered
temperaturemaintained at that temperature for an additional 15 minutes
temperatureAfter cooling the solid
customis recrystallized from a mixture of acetonitrile and water

Sources & evidence

ORD record: ord-6c938f77cc734dd4b30a2cac1a594e71
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04156085

Linked notes

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