Synthesis of 4-chloropyridine

Preparation of 4-chloropyridine

Preparation of 4-chloropyridine

Preparation of 4-chloropyridine

120 g of 1-(4-pyridyl)pyridinium chloride are mixed with 110 g of phosphorus pentachloride and the obtained mixture is melted in an oil-bath at 130-140°. The melt soon solidifies but remelts as the temperature is raised to 150° during 10 min. It is then cooled, treated with ice-water, and made weakly alkaline with sodium carbonate solution. The obtained reaction mixture is thoroughly extracted several times with ether, and the extracts are washed with water and dried over sodium sulfate. The ether is removed by evaporation and the residue is fractionated in a vacuum. Water is added to the distillate, causing a heavy oil to separate, which is taken up in ether, dried, and distilled yielding 30 g of 4-chloropyridine (b.p. 53-55°/20 mm).

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

IUPAC Name

4-chloropyridine

InChI

InChI=1S/C5H4ClN/c6-5-1-3-7-4-2-5/h1-4H

InChI Key

PVMNPAUTCMBOMO-UHFFFAOYSA-N

Canonical SMILES

C1=CN=CC=C1Cl

Depositor-Supplied Synonyms

4-CHLOROPYRIDINE, 626-61-9, Pyridine, 4-chloro-, 4-chloro-pyridine, 4-ChloropyridineHydrochloride, PVMNPAUTCMBOMO-UHFFFAOYSA-N, EINECS 210-956-2, BRN 0105875, p-Chloropyridine, parachloropyridine, 4-chloro pyridine, 4-chloranylpyridine, PubChem23503, AC1L1Z9L, SCHEMBL6842, PVMNPAUTCMBOMO-UHFFFAOYSA-, MolPort-006-112-139, ZINC402776, ACN-C000938, ZINC00402776, AKOS015995550, AM81309, MCULE-4451402923, AJ-21880, AK129898, CJ-03773, HE028167, KB-38295, ZB012945, LS-131067, TX-012033, A9503, FT-0618258, FT-0633358, Z-9580, 176826-EP2281812A1, 5-20-05-00410 (Beilstein Handbook Reference), A833912, W-104969, InChI=1/C5H4ClN/c6-5-1-3-7-4-2-5/h1-4H

Removed Synonyms

4-Chloropyridine hydrochloride, Pyridine, chloro derivs., CID12288, NSC78418, 7379-35-3, 68412-40-8

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