Hydrazinecarboxaldehyde → Formic acid [1-(3-chloro-4-pyridinyl)ethylidene]hydrazide

HRID 1493718Notes

Reaction equation

HRID 1493718 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[Cl:10])(=O)[CH3:2].[CH:11]([NH:13][NH2:14])=[O:12]>C(O)C>[Cl:10][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[C:1](=[N:14][NH:13][CH:11]=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 127424671-(3-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 54167873Formic acid [1-(3-chloro-4-pyridinyl)ethylidene]hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.30 gm (0.0405 mole) of 4-acetyl-3-chloropyridine, 2.46 gm (0.041 mole) of formic acid hydrazide and 100 ml of ethanol was refluxed 18 hr. The mixture was chilled in the freezer to give a solid which was collected in two crops. The product was purified by chromotography [keiselgel 60 (230-400 mesh)] and eluting with 5% methanol/methylene chloride to give 2.56 gm (32%) of white flakes which have a melting point of 175.2° C.

Workup

  1. temperaturewas refluxed 18 hr
  2. temperatureThe mixture was chilled in the freezer
  3. customto give a solid which
  4. customwas collected in two crops
  5. customThe product was purified by chromotography [keiselgel 60 (230-400 mesh)]
  6. washeluting with 5% methanol/methylene chloride
  7. customto give 2.56 gm (32%) of white flakes which

Sources & evidence

ORD record
ord-7f49f73b581a4b498046568cc4e9c92c
Source dataset
uspto-grants-1991_06
Patent number
US05023334

Reaction notes

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