1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine

HRID 335473Notes

Reaction equation

HRID 335473 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:25])[C:13]([N:15]([CH3:24])[N:16]=CC1C=CC=CC=1)=[O:14])[CH3:2]>[Pd].COCCOC>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:25])[C:13]([N:15]([CH3:24])[NH2:16])=[O:14])[CH3:2]

Participants

4

Reactant 1

HCID 666915621-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine

Product 1

HCID 569428781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazineYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 25 mL volume two-necked flask, 1.47 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine ((40-b)-(15)-5), 5.1 ml of 1,2-dimethoxyethane and 147 mg of 5 wt % Pd—C were added. The mixture was stirred under a hydrogen atmosphere at room temperature for 8 hours. An unsolved substance was removed by filtration and washed with 1,2-dimethoxyethane. The filtrates were combined and concentrated under reduced pressure to give 1.068 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39).

Workup

  1. customAn unsolved substance was removed by filtration
  2. washwashed with 1,2-dimethoxyethane
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f89ad93dff134ec0890c8f57f89ba1d2
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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