Hydrochloric Acid → Picolyl chloride hydrochloride

A solution of 200 g (2.15 moles) of 2-methyl-pyridine and 14 g of dimethylformamide in 750 ml chloroform was heated at reflux while 300 g (1.29 mole) of trichloroisocyanuric acid (min. 90% available chlorine) were added thereto in portions without heating over 50 minutes as the reaction mixture remained under reflux by itself. The mixture was stirred for another 2 hours and was cooled and vacuum filtered. The filtrate was washed with 100 ml of 5% sodium hydroxide and the chloroform phase was dried over MgSO4, and filtered. 100 g (2.74 moles) of dry hydrogen chloride were added to the filtrate which was evaporated to dryness under vacuum. The residue was added to 250 ml of dry acetone and the mixture was stirred and vacuum filtered. The precipitate was washed with a little acetone and dried to obtain 185 g of 2-chloromethyl-pyridine hydrochloride. The acetone solution was cooled in the refrigerator to obtain another 42 g product for a total yield of 227 g (64.4%) melting at 120° to 122° C.

1. additionwere added
2. temperaturein portions without heating over 50 minutes as the reaction mixture
3. temperatureunder reflux by itself
4. temperaturewas cooled
5. filtrationvacuum filtered
6. washThe filtrate was washed with 100 ml of 5% sodium hydroxide
7. dry with materialthe chloroform phase was dried over MgSO4
8. filtrationfiltered
9. customwas evaporated to dryness under vacuum
10. additionThe residue was added to 250 ml of dry acetone
11. stirringthe mixture was stirred
12. filtrationvacuum filtered
13. washThe precipitate was washed with a little acetone
14. customdried

ORD record

ord-29a67949f5b842039d4ca96871c9c3a5

Source dataset

uspto-grants-1988_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04719298