NOTES
641from the evaporation of the mixed solvents was then crystallized from methanol, yielding 0.9 g. (47.4%) of pure product, melting at 171-172". And. Calcd. for C18H17NaO:: C. 66.87; H, 5.26; N, 13.00. Found: C, 66.70; H, 5.40; N, 13.11. $?,6-Bis(4'-ethoxy-2'-pyridyl)-4-ethoxypy~dine. To a cooled solution of 0.68 g. of sodium in 91 ml. of anhydrous ethanol was added 2.2 g. of 2,6bis(4'-nitro-2'-pyridyl)-Pnitropyridine. After stirring for 4 hr. at 60-65", solution waa nearly complete. The filtered alcoholio solution was evaporated to dryness using an aspirator and extracted with chloroform. After evaporation to a volume of 45 ml.; 9 ml. of phosphorus trichloride was added and the mixture refluxed for 3 hr. It was then poured on ice and made alkaline. The precipitate obtained, which was insoluble in ether and chloroform was dried and again treated with chloroform and phosphorus trichloride as before. After again pouring on ice and making alkaline, the product dissolved in ether and waa recovered by evaporation of the mixed solvents; yield, 0.8 g. (42.1%) of pure product melting a t 157-158'.
Anal.Calcd. for C,1HpaNnOt: C, 69.04; H, 6.30. Found: C, 68.96; H, 6.49.
2,6-Bis(4'-chloro-b'-pyridyl)-4-chloropyridine.To a SUSpension of 2 g. of 2,6-bis( 4'-nitro-2'-pyridyl)-bnitropyridine in 20 ml. of glacial acetic acid a t 60' was added 12 ml. of acetyl chloride. After heating for 1 hr. on the steam bath, an additional 4 ml. of acetyl chloride was added and heating continued for 1 hr. The mixture was poured on ice and the solution neutralized with sodium bicarbonate. The crude oxide precipitating after separation by filtrat,ion and drying was suspended in 35 ml. of chloroform. To the cold mixture was added 4.5 ml. of phosphorus trichloride. After standing for 1 hr., it was refluxed for one hour on the steam bath, and then poured on ice and made alkaline. The resulting precipitate, after drying, was crystallized from benzene yielding 1.2 g. (75.0%) of product, m.p. 210-211°. An analytical sample melted a t 212-213'.