1,2-Hydrazinedicarboxaldehyde → 6-(1,2,4-triazol-4-yl)-8-methyl-2-(1H)-quinolone

HRID 568365Notes

Reaction equation

HRID 568365 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH:6]=[CH:5]2.[CH:14]([NH:16][NH:17][CH:18]=O)=O>>[N:16]1[N:17]=[CH:18][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([CH3:12])[CH:11]=2)[NH:8][C:7](=[O:13])[CH:6]=[CH:5]3)[CH:14]=1

Participants

3

Reactant 2

HCID 123421,2-HydrazinedicarboxaldehydeHCID 222266466-Amino-8-methylquinolone

Product 1

HCID 144502976-(1,2,4-triazol-4-yl)-8-methyl-2-(1H)-quinolone

Procedure

A mixture of 6-amino-8-methyl-2-(1H)-quinolone (0.485 g) and 1,2-diformylhydrazine (0.245 g) was stirred and heated in a melt at 200° for 1 hour. The residue was then triturated with hot isopropanol, cooled and filtered and the solid residue was recrystallized from chloroform-isopropanol to afford 6-(1,2,4-triazol-4-yl)-8-methyl-2-(1H)-quinolone 0.25H2O, m.p. 369°-371° (0.112 g).

Workup

  1. temperatureheated in a melt at 200° for 1 hour
  2. customThe residue was then triturated with hot isopropanol
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solid residue was recrystallized from chloroform-isopropanol

Sources & evidence

ORD record
ord-b159ef5df0b648dca4ab769fcd20cdb2
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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