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

HRID 127706

Reaktionsgleichung

Reaktionsgleichung von HRID 127706
[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

Komponenten

5

Edukt 3

HCID 75064-CyanopyridineHCID 214504-Aminobenzoic acid hydrazideHCID 5360545Sodium

Produkt 1

HCID 202858124-[5-(Pyridin-4-yl)-1H-1,2,4-triazol-3-yl]anilineAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
245 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5efbdcf11499454da496ac13508bd82f
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256887

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