Vanillin → 2-hydroxy-N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(4-methoxyphenyl)acetamide

HRID 458250Notes

Reaction equation

HRID 458250 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[OH:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:14]([NH:16][NH2:17])=[O:15]>C(O)C>[OH:9][C:8]1[CH:10]=[CH:11][C:3](/[CH:2]=[N:17]/[NH:16][C:14](=[O:15])[CH:13]([OH:12])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:4][C:5]=1[O:6][CH3:7]

Participants

4

Reactant 2

HCID 1183VanillinHCID 13479528Hydroxy-(4-methoxy-phenyl)-acetic acid hydrazide

Product 1

HCID 1360285302-hydroxy-N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(4-methoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Vanillin (23 g, 0.15 mol) is added to a solution of hydroxy-(4-methoxy-phenyl)-acetic acid hydrazide (30 g, 0.15 mol) in 300 ml of ethanol at room temperature. After heating this mixture to reflux for 4 hours, the reaction is poured on water and extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate and evaporated. The residue, which is hydroxy-(4-methoxy-phenyl)-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide, is sufficiently pure to be directly used in the next step.

Workup

  1. temperatureAfter heating this mixture
  2. temperatureto reflux for 4 hours
  3. additionthe reaction is poured on water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7c7168e3a55c4c46aa54477a64b1fe86
Source dataset
uspto-grants-2007_03
Patent number
US07189873B2

Reaction notes

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