2-hydroxy-N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(4-methoxyphenyl)acetamide → hydroxy-(4-methoxy-phenyl)-acetic acid N'-(4-hydroxy-3-methoxy-benzyl)-hydrazide

HRID 458251Notes

Reaction equation

HRID 458251 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[NH:10][C:11](=[O:22])[CH:12]([OH:21])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:23][CH3:24].[H][H]>C(O)C.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][NH:10][C:11](=[O:22])[CH:12]([OH:21])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 1360285302-hydroxy-N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(4-methoxyphenyl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 58679590hydroxy-(4-methoxy-phenyl)-acetic acid N'-(4-hydroxy-3-methoxy-benzyl)-hydrazide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of hydroxy-(4-methoxy-phenyl)-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide (21 g, 63 mmol) in 500 ml of ethanol is hydrogenated under atmospheric pressure with hydrogen and a mixture of 5% of palladium on charcoal (10.5 g) as catalyst. The reaction is stirred for 6 hours at room temperature. Subsequently, the mixture is filtered under argon and the solvent is evaporated to yield hydroxy-(4-methoxy-phenyl)-acetic acid N′-(4-hydroxy-3-methoxy-benzyl)-hydrazide as colourless tarr.

Workup

  1. filtrationSubsequently, the mixture is filtered under argon
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-2005b31a35404372a2cba91eb3fe5172
Source dataset
uspto-grants-2007_03
Patent number
US07189873B2

Reaction notes

Loading…