Onium compounds. XVI. Quaternary derivation of pyridyl ethers was written by Renshaw, R. R.;Conn, R. C.. And the article was included in Journal of the American Chemical Society in 1937.Synthetic Route of C11H9NO This article mentions the following:
The following compounds have been prepared for pharmacol. examination The 2-pyridyl ethers were prepared from 2-C5H4NBr, PhOH and K2CO3 at 200-10° for 3 h. The 4-isomers were obtained by heating 4-pyridylpyridinium dichloride with excess of PhOH and 1.1 mol of its Na salt. 2-PhO, b11 134-5°, 92% yield; 2-o-cresoxy, b21 156-8°, 90%; p-isomer, b22 171.5-2.5°, 92%; m-isomer, b20 164-6°, 83%; 2-carvacroxy, b2 133-4°, 73%; resorcinol di-2-pyridyl ether, b3 183-5°, 38%; 2-pyridyl benzyl ether, b20 162-4°, 65%; 4-BuO, b25 129-31°, 37%; 4-MeO, b31 95-6° (picrate, m. 171-2°); 4-PhO, b21 157-8°; 4-o-, -m- and -p-cresoxy, b19 161-2°, b22 166-7°, b4 124-6°, resp. The onium derivatives were prepared from the ether and alkyl halide in Et2O at room or slightly elevated temperature for from 1 to 6 days. Pyridinium iodides.-2-Phenoxymethyl, m. 174-5°, 96% (all m. ps. corrected); 2-phenoxyethyl, m. 150.5-1.5°, 57%; 2-o-cresoxymethyl, m. 186-6.2° (decomposition), 92%; p-isomer, m. 149-50°, 93%; m-isomer, m. 145-6.5°, 90%; 2-o-cresoxyethyl, m. 122-4°, 69%; m-isomer, m. 126-6.5°, 70%; 2-carvacroxymethyl, m. 134-5°, 85%; 3-phenoxymethyl, yellow, m. 82.5-4°, 96%; 3-phenoxyethyl, m. 136-7°, 98%; 4-phenoxymethyl, m. 227.5-8.5°, 68%; 4-phenoxyethyl, m. 110.5-11°, 70%; 4-o-cresoxy, m. 163-4°, 100%; p-isomer, m. 163°, 81%; m-isomer, m. 157-8°, 92%; 4-o-cresoxyethyl, m. 148°, 79%; p-isomer, m. 126-6.5°, 93%; m-isomer, m. 128°, 85%; 4-p-cresoxy-β-phenoxyethyl (as bromide), m. 129-30°, 64%; 4-m-methoxymethyl, m. 145° (decomposition), 100%; 4-butoxymethyl, m. 74-5°, 100%. N-4′-Pyridyl-4-pyridone forms a chloroaurate, yellow, m. 218-19°, and a chloroplatinate, buff, m. above 300°; di-HCl salt, m. 238° (decomposition) methiodide(N-(4′- methylpyridinium iodide)-4-pyridone), yellowish brown, m. 238-8.5°, 95% yield; ethiodide, with 1 mol H2O, buff m. 134-5°. 3-Phenoxypyridine, b17 147-9°, results in 27% yield from 3-HOC5H4N, 3-KOC5H4N and PhBr with Cu bronze at 200° for 6 h., or in 59% yield from 3-IC5H4N and PhOK in PhOH with Cu bronze (46% with K2CO3). 2-and 4-Phenoxymethylpyridinium iodides are reduced with cleavage of the PhO group, PhOH and N-methylpiperidine being formed. The 3-isomer is readily reduced without the loss of the PhO group (unless in the presence of a large quantity of catalyst); 3-phenoxydimethylpiperidinium iodide, m. 177-8° (corrected). This behavior is general, the stability and aromatic nature of 3-substituted pyridines being quite marked, whereas 2- and 4-pyridyl derivatives are characterized by the lability and often by the anomalous behavior of the substituted groups. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Synthetic Route of C11H9NO).
2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C11H9NO