N-methyl-2-pyrrolidone → 6-Chloro-3-nitropyridine-2-carbonitrile

Temperature

180 °C

2,6-dichloro-3-nitropyridine (5 g, 26 mmol), Cuprous cyanide (4.64 g, 0.59 mml) and appropriate amount of N-methyl pyrrolidone were mixed to form a solution which was heated to 180° C. to react for 15 min, then cooled to 10° C. and poured into ice-water (200 mL) and stirred for 30 min. The solution was then filtered, washed with water and dried. A mixture of the filter cake and Toluene (50 mL) were stirred and heated under reflux for 10 min, then filtered while still hot. Repeated the above operation 3 times, and combined the filtrate. The filtrate was washed with water for 3 times, then with saturated sodium chloride solution for 1 time. The organic phase was dried with anhydrous magnesium sulfate and kept overnight. After filteration, the solution was evaporated under reduced pressure to dryness, and then filtered with a mixture of petroleum ether/aether (4:1) and air-dried to yield 1.78 g of orange yellow solid product with a recovery rate of 37.55%.

1. customto form a solution which
2. customto react for 15 min
3. temperaturecooled to 10° C.
4. filtrationThe solution was then filtered
5. washwashed with water
6. customdried
7. additionA mixture of the filter cake and Toluene (50 mL)
8. stirringwere stirred
9. temperatureheated
10. temperatureunder reflux for 10 min
11. filtrationfiltered while still hot
12. washThe filtrate was washed with water for 3 times
13. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
14. waitkept overnight
15. customAfter filteration, the solution was evaporated under reduced pressure to dryness
16. filtrationfiltered with a mixture of petroleum ether/aether (4:1)
17. customair-dried

ORD record

ord-e13deab80454410ba592ad6fcf056bef

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349835B2