2-Acetyl-4-methylpyridine

Chemical Properties

Crystals

Uses

2-Acetyl-4-methylpyridine may be used in the synthesis of:

• 3,5-bis(4,4"-dimethyl-2,2′:6′,2′′-terpyridin-4′-yl)-1-bromobenzene
• 1,3-bis(4,4"-dimethyl-2,2′:6′,2′′-terpyridin-4′-yl)-5-methylbenzene
• 2-(3′,3′-bis(ethylthio)-1′-oxoprop-2′-en-1′-yl)-4-methylpyridine
• 2-(3′-(N,N-dimethylamino)-1′-oxoprop-2′-en-1′-yl)-4-methylpyridine

Definition

ChEBI: 2-Acetyl-4-methylpyridine is an aromatic ketone.

General Description

2-Acetyl-4-methylpyridine is a substituted pyridine that can be prepared from 2-bromo-4-methylpyridine.

Synthesis

1620-76-4

917-64-6

59576-26-0

GENERAL STEPS: To a stirred mixed solution of 2-cyano-4-methylpyridine (31.19 g, 229 mmol) in anhydrous ethyl ether (300 mL) and anhydrous ethyl ether (230 mL) was slowly added dropwise to an ethyl ether solution of 2M methylmagnesium iodide (149.0 mL, 298 mmol) under nitrogen protection for a controlled time period of 1 hr. The reaction mixture was gradually warmed up to room temperature and continued to stir under nitrogen protection for 1 hour, followed by cooling to 0 °C. An aqueous ammonium chloride solution (120 mL) was slowly added dropwise to the reaction mixture at 0 °C, then the mixture was warmed up to room temperature and stirred for 1 hour. The aqueous layer was separated, the organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel, hexane/ethyl acetate=8:1) to give 16.20 g of 1-(4-methylpyridin-2-yl)ethanone (41) as a yellow oil in 52% yield. The structure of the product was confirmed by 1H NMR (CDCl3, 270 MHz): δ8.54 (1H, d, J=4.9 Hz), 7.88-7.87 (1H, m), 7.30-7.27 (1H, m), 2.72 (3H, s), 2.43 (3H, m).

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 179 - 195
[2] Journal of the American Chemical Society, 1956, vol. 78, p. 5842