Furst, Hans published the artcileAlkylamino pyridines and alkyl pyridine ethers. (Relations between chemical constitution and odor.), Category: ethers-buliding-blocks, the publication is Chemische Technik (Leipzig, Germany) (1958), 693-9, database is CAplus.
The synthesis of alkylandnopyridines and alkyl pyridine ethers was reported. In all cases below are given in parentheses, n20D, b.p./mm., and odor, if any, resp. 2-(Substituted amino)-pyridines were prepared by the method of Sharp (C.A. 34, 16638) in 30-70% yield (substituents given: iso-Bu (1.5328, 69°/2, mignonette); n-hexyl (-,111°/2, strong mignonette); phenylethyl (-, 158°/3, weak mignonette); Et, Bu (1.5251, 125°/2, strong salicylic, ester); ethyl, n-decyl (1.5085, 132°/2, weak); ethyl, benzyl (1.5947, 112°/2, weak mignonette). 2-Methyl-6-(substituted amino)pyridine derivatives were prepared from 2-methyl-6-aminopyridine by the Tschitschibabin procedure in 80% yields: Bu (1.5329, 82°/2, earthy); iso-Am (1.5170, 91°/2, penetrating); n-hexyl (1.5205, 108°/2, weak mignonette); Et, Bu (1.5195, 85°/1, earthy); n-Pr, Bu (1.5153, 90°/1, weak mignonette); n-hexyl, Bu (1.5063, 112°/1, weak earthy). Also prepared were 2,6-Pr(PrBuN)C5H3N (1.5142, 90°/1, burnt), and 2,6-Bu(PrBuN)C5H3N (1.5138, 104°/1, burnt). 3-Methyl-6-(substituted amino)pyridine derivatives, in about 80% yields, were prepared according to the method of Stuart: Bu (1.5351, 74°/2, mignonette); n-hexyl (1.5250, 98/2, woody); benzyl (-, 122°/2, earthy, m. 76°); Et, Bu (1.5129, 72°/1, weak mignonette). 4-Methyl-6-(substituted amino)pyridine derivatives were prepared from 4-methyl-6-aminopyridine: Bu(-, 82°/2, flowery, m. 41°); iso-Bu (1.5348, 75°7/2, rooty); benzyl (-, -, weak mignonette, m. 76°); Et, Bu (1.5197, 82°/1, weak mignonette). 2-Pyridyl alkyl ethers were prepared from 2-bromopyridine and the alcs. in 60% yields (alkyl given): n-hexyl (1.4878, 73°/2, fruity); n-heptyl (1.4850, 83°/2, pleasant); isoöctyl (1.4825, 85°/2, fruity); cyclohexyl (1.5242, 65°/2, -). 2-Alkyl-6-pyridyl alkyl ethers were prepared from the corresponding ethers, NaNH2, and the alkyl halides in 70% yields: 2-(n-butyl)-6-pyridyl, n-hexyl (1.5186, 72°/0.5, burnt); 2-(n-amyl)-6-pyridyl, n-heptyl (1.5123, 85°/0.5, celery); 2-isohexyl-6-pyridyl, n-amyl (1.4900, 98°/0.5, weak elder); 2-(n-nonyl)-6-pyridyl, n-amyl (1.4859, 130°/0.5, weak elder). 2-Methyl-6-(R-substituted)pyridine derivatives (R = alkyl or aryl) were prepared from 2,6-dimethylpyridine and R halide plus NaNH2: Am (1.4869, 69°/2, rooty); n-hexyl (1.4867, 79°/2, rooty); n-heptyl (1.4854, 89/2, pea-like); cyclohexyl (1.5185, 75°/2, fatty); benzyl (1.5644, 94°/2, fruity). 2-Methyl-6-alkyl-pyridines were also prepared as above: isohexyl (1.4858, 52°/2, rooty), n-heptyl (1.4820, 65°/2, pealike); n-nonyl (1.4826, 85°/2, fatty); and phenylethyl (1.5679, 91°/2, fruity and leafy).
Chemische Technik (Leipzig, Germany) published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Category: ethers-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem