Hydroxylamine → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine

HRID 335478Notes

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:22])[C:13]([N:15]([CH3:21])[N:16]=CC(C)C)=[O:14])[CH3:2].NO>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:22])[C:13]([N:15]([CH3:21])[NH2:16])=[O:14])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 25 mL volume three-necked flask, 1.0 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(2-methyl-1-propylidene)hydrazine ((40-b)-(15)-4), 3.8 ml of methanol and 330 mg of 50 wt % hydroxylamine aqueous solution were added, and the mixture was stirred at 50° C. for 2.5 hours and then 60° C. for 14.5 hours. The reaction mixture was concentrated under reduced pressure and water and t-butyl methyl ether were added to the residue. The precipitated crystals were collected by filtration, washed with hexane and dried to give 0.63 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39).

Workup

wait60° C. for 14.5 hours
concentrationThe reaction mixture was concentrated under reduced pressure and water and t-butyl methyl ether
additionwere added to the residue
filtrationThe precipitated crystals were collected by filtration
washwashed with hexane
customdried

Sources & evidence

ORD record: ord-2b74691bcded4bcca2cdfc42bbe9d075
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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