4-Acetylpyridine → 2-Methylbenzoic acid [1-(4-pyridinyl)ethylidene]hydrazide

HRID 1493687Notes

Reaction equation

HRID 1493687 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C:10]1([CH3:20])[C:11]([C:16]([NH:18][NH2:19])=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=1>C(O)C>[N:7]1[CH:8]=[CH:9][C:4]([C:1](=[N:19][NH:18][C:16](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH3:20])[CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 142824-AcetylpyridineHCID 82110o-Toluohydrazide

Product 1

HCID 36012992-Methylbenzoic acid [1-(4-pyridinyl)ethylidene]hydrazideYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.63 gm (0.03 mole) of 4-acetylpyridine, 4.51 gm (0.03 mole) of o-toluic acid hydrazide and 100 ml of 95% ethanol is refluxed 8 hr. The hot solution is filtered. The filtrate is diluted with water to the cloud point and cooled to room temperature. The mixture is chilled in the refrigerator and the product collected, washed with water, and dried to yield 4.78 gm (63%) of the title compound having a melting point of 187.4° C.

Workup

  1. temperatureis refluxed 8 hr
  2. filtrationThe hot solution is filtered
  3. additionThe filtrate is diluted with water to the cloud point
  4. temperatureThe mixture is chilled in the refrigerator
  5. customthe product collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ff87bbd7b41b4f2b9e77c06274e976a4
Source dataset
uspto-grants-1991_06
Patent number
US05023334

Reaction notes

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