メチルピリヂン誘導体の合成 (I)
1951 年 71 巻 3 号 p. 156-160
詳細
1951 年 71 巻 3 号 p. 156-160
Some 2, 6-lutidine derivatives were synthesized from 4-nitro-2, 6-lutidine-N-oxide. Reduction of 4-nitro-2, 6-lutidine-N-oxide in acetic anhydride with Pd-charcoal as a catalyst, results in absorption of 3mol. of hydrogen, but after that, the speed of reduction becomes slow. Addition of Pt-oxide allows a further absorption of 1mol. of hydrogen smoothly and 4-amino-2, 6-lutidine (prisms, m.p. 191-192°) was obtained. 4-Nitro-2, 6-lutidine-N-oxide was treated in alcoholic solution with sodium methoxide to yield 4-methoxy-2, 6-lutidine-N-oxide (prisms, m.p. 69-70°), catalytic reduction of which by Pd-charcoal in acetic anhydride gave 4-methoxy-2, 6-lutidine. Its ethobromide condensed smoothly with benzaldehyde or anisaldehyde in alcoholic solution with piperidine as a catalyst, giving 4-methoxy-2, 6-distyrilpyridine ethobromide (yellow needles, m.p. 249°) or 4-methoxy-2, 6-di-(p-methoxy-styril)-pyridine ethobromide (yellow needles, m.p. 250°), respectively. The corresponding N-oxide was inactive in condensation reaction with benzaldehyde.
