Synthesis of 1-(4-pyridyl)pyridinium chloride hydrochloride

Preparation of 1-(4-pyridyl)pyridinium chloride hydrochloride

Preparation of 1-(4-pyridyl)pyridinium chloride hydrochloride

Preparation of 1-(4-pyridyl)pyridinium chloride hydrochloride

200 g of pyridine (dried over potassium hydroxide) are dropped, with stirring and ice-cooling, into 600 g of thionyl chloride by maintaining the temperature at 8-12°. The obtained mixture is stirred for some hours while the inner temperature is allowed to rise slowly to 20° and then set aside at 20° for 3 days. The excess of thionyl chloride is distilled off in a vacuum and the residue is heated for an hour on a boiling water-bath. The resulting greyish-brown crystalline mass is cooled to 0°, triturated with 250 ml of ice-cold dry ethanol (ice-cooling!), filtered off, washed twice with ice-cold dry ethanol, dried in a vacuum, and dissolved in a mixture of 100 ml of water and 300 ml of 2N hydrochloric acid. The obtained solution is boiled for 5 min with active charcoal, concentrated in vacuum to the volume of 180 ml, and cooled to 0°. Pale yellow 1-(4-pyridyl)pyridinium chloride hydrochloride separates, the obtained crystals are washed with dry ethanol and dried in a vacuum, yielding 167 g of the title compound (m.p. 158-160°).

Ber. Deut. Chem. Ges., 64, 1052 (1931).
J. Chem. Soc, 1954, 1796.

IUPAC Name

4-pyridin-1-ium-1-ylpyridine;chloride;hydrochloride

InChI

InChI=1S/C10H9N2.2ClH/c1-2-8-12(9-3-1)10-4-6-11-7-5-10;;/h1-9H;2*1H/q+1;;/p-1

InChI Key

QZOFFMRDIRXGKJ-UHFFFAOYSA-M

Canonical SMILES

C1=CC=[N+](C=C1)C2=CC=NC=C2.Cl.[Cl-]

Depositor-Supplied Synonyms

5421-92-1, 1-(4-Pyridyl)pyridinium chloride hydrochloride, [1,4′-Bipyridin]-1-ium chloride hydrochloride, 1,4′-Bipyridinium, chloride, n-(4-pyridyl)pyridinium chloride hydrochloride, 1-(4-Pyridinyl)pyridinium chloride hydrochloride, SBB057622, 1,4′-Bipyridinium, chloride, hydrochloride, 1-(4-PYRIDYL)PYRIDINIUM CHLORIDE HCl, 4-pyridin-1-ium-1-ylpyridine chloride hydrochloride, 1,4′-Bipyridinium, chloride, hydrochloride (1:1:1), 4-pyridylpyridine, chloride, chloride, N-[4-pyridyl]pyridinium chloride hydrochloride, ACMC-20akax, PubChem15356, AC1L2XFY, 1, chloride, hydrochloride, AC1Q1S1D, P71517_ALDRICH, SCHEMBL1416747, 4-Pyridiniopyridinium dichloride, CTK3J1269, N- pyridiniumchloridehydrochloride, NSC1909, MolPort-003-939-208, QZOFFMRDIRXGKJ-UHFFFAOYSA-M, KST-1B8298, NSC 1909, NSC-1909, EINECS 226-543-5, AR-1B7494, AKOS015891505, LS41180, MCULE-7622929607, RP18061, RTR-019172, TRA0058859, 4-Pyridylpyridinium chloride hydrochloride, AK116754, HE003229, I090, KB-64004, DB-052517, ST2420039, TL8006908, TR-019172, FT-0602263, P0565, ST51006724, 1-(4-Pyridyl)pyridiniumchloride hydrochloride, N-[4-pyridyl] pyridinium chloride hydrochloride, A830042, I02-0442, W-105655, 4-(1-pyridin-1-iumyl)pyridine chloride hydrochloride, 1-(4-Pyridinyl)pyridinium chloride hydrochloride (1:1:1), 1-(pyridin-4-yl)-1$l^{5}-pyridin-1-ylium chloride hydrochloride, 149764-60-3

Removed Synonyms

C10H10Cl2N2, CID79461, 74404-39-0, 71643-74-8

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