4-Methoxybenzohydrazide → HCID 54345301, compound

HRID 1608181Notes

Reaction equation

HRID 1608181 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([NH:21][NH2:22])=[O:20])=[CH:17][CH:16]=1>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[N:22][NH:21][C:19](=[O:20])[C:18]1[CH:23]=[CH:24][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 767924-MethoxybenzohydrazideHCID 796192-Quinolinecarboxaldehyde

Product 1

HCID 54345301HCID 54345301, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.14 gm (0.02 mole) of 2-quinolinecarboxaldehyde, 3.32 gm (0.02 mole) of 4-methoxybenzhydrazide and 100 ml of ethanol is refluxed for 9 hrs. The hot solution is filtered and cooled slowly to room temperature. The mixture is chilled. The crystals which separate are collected. The crude mixture is crystallized from ethyl acetate and recrystallized from tetrahydrofuran to yield 3.0 gm (49%) of title compound, having a melting point of 220°-222° C.

Workup

  1. temperatureis refluxed for 9 hrs
  2. filtrationThe hot solution is filtered
  3. temperatureThe mixture is chilled
  4. customThe crystals which separate
  5. customare collected
  6. customThe crude mixture is crystallized from ethyl acetate
  7. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-e0acb9a3002d4cbf992ce0ef923a9ad5
Source dataset
uspto-grants-1989_09
Patent number
US04870082

Reaction notes

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