Acetone, 1 - phenylhydrazone

To a stirred solution containing 49 gm (0.11 mole) of lead tetraacetate (supplied as a 90% solution in acetic acid) in 200 ml of methylene chloride is added a solution of 14.8 gm (0.10 mole) of acetone phenylhydrazone in 25 ml of methylene chloride over a 15 min period while maintaining the reaction temperature between 0° and 10°C with an ice bath. After the addition has been completed, the reaction temperature is raised to 20°-25°C and stirring is continued for an additional 15 min. Then to the reaction mixture is added 200 ml of water, the inorganic solids are filtered off, and the methylene chloride layer is separated. This product layer is washed in turn with water and with dilute aqueous sodium bicarbonate until all the acetic acid has been removed. After drying the methylene chloride solution with anhydrous sodium sulfate, the solvent is evaporated off at reduced pressure. The residue is distilled under reduced pressure. The product has b.p. 89°C (1 mm Hg) yield 17.0 gm (83 %). 

The phenylhydrazone of acetone was hydrogenated to form A -isopropyl-/V-phenylhydrazine over colloidal platinum. However, a similar hydrazone, l-(/V-acetyl-2-piperidyl)acetone phenylhydrazone, was hydrogenated and hydrogenolyzed to form l-(/V-acetyl-2-piperidyl)-2-aminopropane in good yield. ... 

Fischer indole synthesis. The synthesis of a 2-substituted indole by the method of Fischer " can be interpreted as shown in the formulation. An Organic Syntheses preparation of 2-phenylindole specified heating acetone phenylhydrazone with five times its weight of zinc chloride al 170° and adding 4 parts of sand to prevent solidification on cooling (yield of 2-phenyllndole 72-HO%). Chapman el /. studied various cyclizing agents (coped, hydrochloric acid, dry HCI, BFn. polyphosphoric... 

Difluoramine reacts vigorously with acetone phenylhydrazone to give N-fluoro-dimethylketimine.8... 

An acidic ion-exchange resin, Amberlite IR-120, was also employed by Yamada et al. to effect the cyclization of the phenylhydrazones of ketones including ethyl-methyl ketone, propiophenone, and cyclohexanone in water under reflux [15]. Yields of 60-90% were obtained but acetone phenylhydrazone proved unreactive under these conditions. 

Propanone phenylhydrazone Acetone, phenylhydrazone C9H12N2 103-02-6 148.204 orth 42 163 " s EtOH, eth, dll acid... 

We attempted to oxidize acetone phenylhydrazone 83 with MCPBA in CH2CI2 at -65 °C but... 

Two other drugs that are more efficient as lipoxygenase than as cyclooxygenase inhibitors are benoxaprofen [401] and acetone phenylhydrazone [399]. Benoxaprofen inhibits the lipoxygenases of ionophore stimulated rabbit PMNL with an ICj of 6x 10 M [401,402]. Acetone phenylhydrazone inhibits platelet 12-lipoxygenase, IC5o= 1-6 X 10 M [403]. 

N.N -Benzenyl- [a.a -diamino-aceton]-phenylhydrazon 24,168. 4-[4-Ammo-aniUno]-3-methyl-t-phenyl. pfTazol 26 I 819. 

Cs 1H4 5Cli,N3P2Pt, cis-Chlorobis( triphenylphosphine) - (1,3-di-p-tolyl-triazenido)platinum(II) chloroform solvate, 42B, 874 Cs1H4 5N3OP2RU, Hydrido(1,3-di-p-tolyltriazenido)bis(triphenylphos-phine)ruthenium(II) carbonyl, 42B, 874 Cs iHi, 9BF N2P2Pt, trans Hydrido(acetone phenylhydrazone)bis(triphen-ylphosphine)platinum(lI) tetrafluoroborate benzene, 43B, 1343 CsiH62AsBNnNiS, Isothiocyanato-(N,N-bis-(2-(diethylamino)ethyl)-2-(diphenylarsino)ethylamine-N,N,N)-nickel(II) tetraphenylborate,... 

K-thiocyanate in water added slowly to a soln. of acetone phenylhydrazone in glacial acetic acid, warmed to 50-60°, then allowed to cool slowly, and the product isolated after ca. 1 hr. 3,3-dimethyl-l-phenyl-l,2,4-triazolidine-5-thione. Y 89%. F.e. s. H. Sdiildknedit and G. Renner, A. 761, 189 (1972). 

Acetone phenylhydrazone allowed to react in methanol with iodine in the presence of Na-acetate 2-phenylazo-2-methoxypropane. Y 50%. F. e. s. J. Sdiantl, Tetrah. Let. 1970, 3785. 

Excess acetone phenylhydrazone allowed to react with difluoroamine in vacuo N-fluorodimethylketimine. Y 30-50%. C. L. Bumgardner and J. P. Freeman, Tetrah. Let. 1966, 5547. 

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