2-Methyl-1-(3-nitrophenyl)-1-propanone → 2-Methyl-1-(3-nitrophenyl)-1-propanone hydrazone

To a partially dissolved solution of 2-methyl-1-(3-nitrophenyl)-1-propanone (Preparation 55, 1.0 g, 5.2 mmol) in industrial methylated spirits (6 ml) was added dropwise hydrazine hydrate monohydrate (0.5 ml, 10.4 nmuol). The reaction mixture was refluxed for 16 h, before cooling to room temperature and pouring into ice and water (50:50, 15 ml) giving a very fine white precipitate in a yellow solution. The mixture was extracted with diethyl ether (2×50 ml), the combined organic extracts were washed with brine and dried (MgSO4), before concentrating to give an amber oil. The crude product was purified by chromatography on silica gel cluting with dichloromethane:ethyl acetate (19:1) to give the title compound as a mixture of cis and trans hydazones (0.54 g, 50%).

1. temperatureThe reaction mixture was refluxed for 16 h
2. customgiving a very fine white precipitate in a yellow solution
3. extractionThe mixture was extracted with diethyl ether (2×50 ml)
4. washthe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. concentrationbefore concentrating
7. customto give an amber oil
8. customThe crude product was purified by chromatography on silica gel cluting with dichloromethane:ethyl acetate (19:1)

ORD-Eintrag

ord-bd78f6503b0c47e1b886e1148d54d7b6

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06313312B1