2-Quinolinecarboxaldehyde → 3-Nitrobenzoic acid (2-quinolinylmethylene)hydrazide

HRID 1608182Notes

Reaction equation

HRID 1608182 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.[N+:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([NH:21][NH2:22])=[O:20])([O-:15])=[O:14]>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][CH:25]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1

Participants

4

Reactant 2

HCID 796192-QuinolinecarboxaldehydeHCID 32914983-Nitrobenzohydrazide

Product 1

HCID 542356113-Nitrobenzoic acid (2-quinolinylmethylene)hydrazideYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.00 gm (0.019 mole) of 2-quinolinecarboxaldehyde, 3.44 gm (0.019 mole) of m-nitrobenzhydrazide 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 product is recrystallized from tetrahydrofuran to yield 3.04 gm (50%) of the title compound, having a melting point of 217°-218° 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 product is recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-7590e77d53654501964a0e2455434285
Source dataset
uspto-grants-1989_09
Patent number
US04870082

Reaction notes

Loading…