1-Chloro-4-(chloromethyl)benzene → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine

To a suspension of 4-methoxyphenylhydrazine hydrochloride (41 g, 230 mmol) in methylene chloride (1000 ml) under nitrogen were added diisopropylamine (79.8 g, 612 mmol), 4-chlorobenzylchloride (40.25 g, 250 mmol) and tetrabutylammonium bromide (22.8 g, 70 mmol). The resulting mixture was stirred at ambient temperature for 48 hours. The reaction mixture was then washed with water, and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2.5% methanol in methylene chloride) followed by washing of the solid with 10% ethyl ether in hexane and drying in vacuo to provide 43.5 g of 1-(4-chlorobenzyl)-1-(4methoxyphenyl)hydrazine, mp. 55° C.

1. washThe reaction mixture was then washed with water, and brine
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was purified by column chromatography (silica gel, 2.5% methanol in methylene chloride)
6. washby washing of the solid with 10% ethyl ether in hexane
7. customdrying in vacuo

ORD-Eintrag

ord-d8ce271105e24509955cfcff1c341e5f

Quelldatensatz

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05420282