4-Pyridinecarboxaldehyde → Diphenylmethyl 2-(4-pyridinylmethylene)hydrazinecarboxylate

HRID 1493697Notes

Reaction equation

HRID 1493697 reaction equation
[C:1]([O:5][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[NH:2][NH2:3].[N:19]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=1>C(O)C>[N:19]1[CH:24]=[CH:23][C:22]([CH:25]=[N:3][NH:2][C:1]([O:5][CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:4])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 76944Hydrazinecarboxylic acid, diphenylmethyl ester

Product 1

HCID 54486556Diphenylmethyl 2-(4-pyridinylmethylene)hydrazinecarboxylateYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 24.11 gm (0.1 mole) of benzhydryl carbazate in 200 ml of warm absolute ethanol is added 10.66 gm (0.1 mole) of 4-pyridinecarboxaldehyde in 75 ml of absolute ethanol. The mixture is refluxed 7 hr and cooled. The solvent is removed in vacuo. Recrystallization from ethanol/Skellysolve B yields 26.03 gm (78.5%) of the title compound having a melting point of 159°-160° C.

Workup

  1. temperatureThe mixture is refluxed 7 hr
  2. temperaturecooled
  3. customThe solvent is removed in vacuo
  4. customRecrystallization from ethanol/Skellysolve B

Sources & evidence

ORD record
ord-475c9c852a67464cac1643d9ef599f05
Source dataset
uspto-grants-1991_06
Patent number
US05023334

Reaction notes

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