含窒素環化合物の合成 (第76報)
フェニルピリジルエーテル類について その5
1952 年 72 巻 9 号 p. 1137-1140
詳細
1952 年 72 巻 9 号 p. 1137-1140
1) Nitration of phenyl pyridyl-(2) ether with sulfuric and nitric acids gives 2, 4-dinitrophenyl compound when the reaction is carried out at above 50° and a 4-nitrophenyl compound when reacted at 30-35°. Application of piperidine to these nitrophenyl pyridyl-(2′) ethers results in decomposition to form nitrophenylpiperidines.
2) By the condensation of alkali salts of o-, m- and p-nitrophenol to 2-bromopyridine, 2-, 3- and 4-nitrophenyl pyridyl-(2′) ethers were respectively obtained.
3) Application of hydrogen sulfide to 4-nitrophenyl 5′-nitropyridyl-(2′) ether in alcoholic ammonia solution results in its reduction to 4-nitrophenyl 5′-aminopyridyl-(2′) ether. The latter, by diazotization and deamination, changes to 4-nitrophenyl pyridyl-(2′) ether. Catalytic reduction of 4-nitrophenyl 5′-nitropyridyl-(2′) ether with palladium-carbon yields 4, 5′-diamino derivative.
4) 4-Amino (acetamino) phenyl 5′-nitropyridyl-(2′) ethers were prepared by the condensation of 2-chloro-5-nitropyridine and alkali salt of p-amino- or p-acetaminophenol.
