NOTES
5796
VOl. 74
Experimental and of their respective acetates. The production of 5-hydroxy-7-methoxy-2,U-dimethylchromonc To a stirred and chilled solution of 11 g. of sodium metain 150 cc. of water, 100 cc. of ammonium hydroxide from 5,7-dihydroxy-2-methylchrornone in this man- periodate was added slowly until the precipitate first formed went into ner is in accordance with the well established be- solution. Usually a crystal mass separated on continued havior of phloroglucinol and its derivatives6 and in- cooling. A solution of 6.5 g. of crude nicotinyl hydrazide in 75 cc. dicates the accuracy of the formulation (V) for the about 8% amnionium hydroxide was added t o the stirred methylation product of genistein (IV) obtained un- of ice-cold periodate solution as rapidly as the gas evolution der similar conditions.' Confirmation of the struc- permitted. Stirring and cooling were continued for five ture (V) will be provided in a forthcoming publica- minutes, the mixture was allowed to stand for 15 more minutes, and then precipitated with a solution of 12 g. of tion. Experimental
5-Hydroxy-7-methoxy-2,6-dimethylchromone.-A solution of 5,7-dihydroxy-2-metliylchromone(0.5 g. ) in rnethaiiol (10 ml.) and methyl iodide (10 nil.) containing sodiuni (0.2 g . ) was refluxed during 12 hours, when most of the solvent was removed under reduced pressure. Addition of water (50 ml.) and excess 3 &Vhydrochloric acid to the residue furnished a crystalline precipitate which after purification from methanol gave rise t o eugciiitin (0.4 g.) in colorless needles, m . p . 162-103", undepressed on admixture with :in authentic specimen aiid eshibiting an intense bluc ferrir reaction in alcohol. A n a l . Calcd. for C111190d(OMc): C, 65.14; 13, 5.1'3; OMc, 14.09. Found: C, 65.35; I i , L 7 4 ; OMr, 1.3.24, The acetnte, prepared by the sodium acetateeacctic anhydride method had 1n.p. 171' alone or in admixture with nil :tuthcntic speciiiicm.
Acknowledgment.-The author thanks Smith, Kline 8z French Laboratories for the hospitality of their laboratories, where most of this work was perfornied, Mrs. Rita Preis for the analysis, A h - . Samuel Rump for the ultraviolet absorption curves which were determined in methanol solution using a Cary recording quartz spectrophotometer, Model 1 1 11, arid Professor H . Schmid for specimens of natural eugenitiri and thc acetate. h g., F. I1 C u r d a n d A . K o b e r t s o ~ i J. . Cliem. Stir 17, 'A? Baker arid R . R ~ ~ l ~ i i i sibiti., o n , 2713 (l!l26!.
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' Y I E L-NIVERSITY O F I.IVERPOOL, E S G L A N D A N I ) SXITII, KLIXE & F R E S C l l ~JAIIOKATORIES,~ ' I I I I . A D E L P I ~ I A ,1'A
The Preparation of Nicotinaldehyde 1%"11. N,~ ~ I N G F I E L lv. I ~ , I
