Hydrochloric Acid → 2-Chloro-1-(pyridin-3-yl)ethan-1-one--hydrogen chloride (1/1)

To a solution of 100 g (0.83 moles) of 3-acetylpyridine in diethyl ether (1 L) was added of 1 M hydrogen chloride in ether (950 mL) with rapid stirring. The precipitated solids were filtered, washed with ether and dried. The hydrochloride salt (129 g, 0.83 moles) was added to a 5 L reactor equipped with a mechanical stirrer and dissolved with 1 M hydrogen chloride in acetic acid (830 mL). The mixture was stirred until a clear solution was obtained. N-chlorosuccinimide (111 g, 0.83 moles) was added, and a yellow mixture resulted. The solution was stirred at room temperature for 18 hours, gradually becoming a colorless suspension. The solids were collected by filtration and washed with ether. The filtrate was treated overnight with 80 g of N-chlorosuccinimide and additional product was collected to give a combined yield of 152 g. 1H NMR (DMSO-d6) δ 10.3 (br s, 1 H), 9.27 (s, 1 H), 8.96 (d, J=5.1 Hz, 1 H), 8.62 (d, J=9.9 Hz, 1 H), 7.89 (m, 1 H), 5.30 (s, 2 H); MS (EI) m/z 155 (M+).

1. filtrationThe precipitated solids were filtered
2. washwashed with ether
3. customdried
4. customequipped with a mechanical stirrer
5. customwas obtained
6. customa yellow mixture resulted
7. stirringThe solution was stirred at room temperature for 18 hours
8. filtrationThe solids were collected by filtration
9. washwashed with ether
10. additionThe filtrate was treated overnight with 80 g of N-chlorosuccinimide and additional product
11. customwas collected
12. customto give a combined yield of 152 g

ORD record

ord-5d65c980085b48bfa2bcd1b1decf3fa2

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06051586