Toluene → 2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazide

HRID 335464

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:18])[C:13](OCC)=[O:14])[CH3:2].C1(C)C=CC=CC=1.O.[NH2:27][NH2:28]>O>[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:18])[C:13]([NH:27][NH2:28])=[O:14])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a 100 mL volume three-necked flask, ethyl 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetate ((9-a) (10.0 g)) and toluene (35 ml) were added. Hydrazine hydrate (2.13 ml) was added dropwise thereto at 60° C. and the obtained mixture was stirred at 70° C. for 7 hours. The reaction mixture was cooled to room temperature, water was added thereto and the organic layer was removed. The aqueous layer was extracted with toluene. The organic layers were combined and concentrated under reduced pressure to give 9.40 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetohydrazide ((12-1)-(11)-39).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe organic layer was removed
extractionThe aqueous layer was extracted with toluene
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cd240b7a84414d0a9629b9b3cbb75b72
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Linked notes

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