benzyl N'-[3-methoxy-4-(4-methylimidazol-1-yl)benzoyl]hydrazinecarboxylate → 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide

HRID 406381Notes

Reaction equation

HRID 406381 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1)[C:6]([NH:8][NH:9]C(OCC1C=CC=CC=1)=O)=[O:7]>CO.[OH-].[Pd+2].[OH-].[C]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1)[C:6]([NH:8][NH2:9])=[O:7]

Participants

4

Reactant 1

HCID 66618835benzyl N'-[3-methoxy-4-(4-methylimidazol-1-yl)benzoyl]hydrazinecarboxylate

Product 1

HCID 666078503-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazideYield 102.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl N′-[3-methoxy-4-(4-methylimidazol-1-yl)benzoyl]hydrazinecarboxylate (1.25 g) in methanol (60 mL) was added 20% palladium hydroxide-carbon (50% wet, 250 mg) and the mixture was hydrogenated at an intermediate pressure (3.8 atm) for two hours and 30 minutes. The palladium-carbon was removed by filtration through celite. The filtrate was concentrated under reduced pressure to obtain 826 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customThe palladium-carbon was removed by filtration through celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ad266442a6547fd9444d15ef6eb21a6
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…