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

HRID 579288Notes

Reaction equation

HRID 579288 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:17])[C:13]([NH:15][NH2:16])=[O:14])[CH3:2]>CO>[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:17])[C:13]([NH:15][N:16]=[CH:1][CH:3]([CH3:8])[CH3:4])=[O:14])[CH3:2]

Participants

3

Reactant 1

HCID 569428732-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazide

Product 1

HCID 682980701-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(2-methyl-1-propylidene)hydrazineYield 188.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 300 mL volume three-necked flask, 20.0 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetohydrazide ((12-1)-(11)-39), 76 ml of methanol and 12.3 g of isobutylaldehyde were added and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure and then hexane was added thereto. The precipitated crystals were collected by filtration and dried under reduced pressure to give 23.2 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(2-methyl-1-propylidene)hydrazine ((40-a)-(14)-4).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionhexane was added
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4b4c56d60b7b48c5907de91826becd1e
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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