Ethanol → 2-Methylcyclopropanecarboxylic acid [1-(3-pyridinyl)propylidene]hydrazide

HRID 1085969Notes

Reaction equation

HRID 1085969 reaction equation
[CH3:1][CH:2]1[CH2:4][CH:3]1[C:5]([NH:7][NH2:8])=[O:6].[CH2:9]([C:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=O)[CH3:10].CCO.CCCCCC.C(OCC)(=O)C>C(O)(=O)C.CCOCC>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11](=[N:8][NH:7][C:5]([CH:3]2[CH2:4][CH:2]2[CH3:1])=[O:6])[CH2:9][CH3:10])[CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 449292-Methylcyclopropane-1-carbohydrazideHCID 740741-(3-Pyridyl)propan-1-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 544792022-Methylcyclopropanecarboxylic acid [1-(3-pyridinyl)propylidene]hydrazideYield 29.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8.0 gm (0.07 mole) of 2-methylcyclopropanecarboxylic acid hydrazide, 9.46 gm (0.07 mole) of ethyl-3-pyridyl ketone, 10 drops of glacial acetic acid and 100 ml of EtOH was refluxed 20 hr. Tlc (9:1 Skellysolve B/Ethyl acetate on silica gel) shows no remaining starting material. The reaction mixture was cooled to room temperature and evaporated in vacuo to give a liquid. The liquid solidified on standing. The solid was slurried in ether, collected and dried to give 4.77 gm (29%) of the title compound having a melting point of 137.3° C.

Workup

  1. temperaturewas refluxed 20 hr
  2. customevaporated in vacuo
  3. customto give a liquid
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-595548edce3d4c7c803402bdd49d91a4
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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