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

HRID 1085936Notes

Reaction equation

HRID 1085936 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-5d3f93b6117547329aa0f88c43bf3130
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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