1,2-Hydrazinedicarboxaldehyde → 4,5-dihydro-6-[4-(4H-1,2,4-triazol-4-yl)phenyl]-3(2H)-pyridazinone

HRID 569770Notes

Reaction equation

HRID 569770 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH:15]([NH:17][NH:18][CH:19]=O)=O>>[N:17]1[N:18]=[CH:19][N:1]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)[CH:15]=1

Participants

3

Reactant 2

HCID 123421,2-HydrazinedicarboxaldehydeHCID 108670826-(4-aminophenyl)-2H-pyridazin-3-one

Product 1

HCID 140994344,5-dihydro-6-[4-(4H-1,2,4-triazol-4-yl)phenyl]-3(2H)-pyridazinone

Conditions

Temperature
220 °C

Procedure

A mixture of 6-(4-aminophenyl)-3(2H)-pyridazinone (3.78 g, 0.02 mol) and diformylhydrazine (1.76, 0.02 mol) are heated together at 220° C. for six hours. The solid mass is chromatographed and finally crystallized from acetonitrile/methanol to yield the product 4,5-dihydro-6-[4-(4H-1,2,4-triazol-4-yl)phenyl]-3(2H)-pyridazinone, mp 292.5°-293° C. (dec).

Workup

  1. customThe solid mass is chromatographed
  2. customfinally crystallized from acetonitrile/methanol

Sources & evidence

ORD record
ord-509a0f39318f432cbae08f72e11612d3
Source dataset
uspto-grants-1988_03
Patent number
US04734415

Reaction notes

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