Dimethyl Sulfate → 6-Methyl-4-nitropyridine-2-carbonitrile

Temperature

70 °C

To 10.2 ml (13.5 g, 104 mmol, 1.1 equiv.) of dimethylsulfate were added 15.0 g (94.4 mmol) of 2-Methyl-4-nitropyridine-N-oxide at 60° C. The reaction mixture was then stirred for 90 min at 70° C., and allowed to cool to room temperature. The solidified residue was triturated with 30 ml of ether. The product was filtered, washed with 20 ml of ether, and dried. The product was then dissolved in 100 ml of water and added dropwise over a period of 30 min. to a at −8° C. cooled solution of 24.6 g (377 mmol, 4.0 equiv.) of potassium cyanide in 100 ml of water. The reaction mixture was stirred for a further 15 min. at −8° C. The product was filtered off, washed twice with 15 ml of water and dried in vaccuo to yield the title compound (11.1 g, 72%) as a light brown solid.

1. temperatureto cool to room temperature
2. customThe solidified residue was triturated with 30 ml of ether
3. filtrationThe product was filtered
4. washwashed with 20 ml of ether
5. customdried
6. dissolutionThe product was then dissolved in 100 ml of water
7. additionadded dropwise over a period of 30 min. to a at −8° C.
8. stirringThe reaction mixture was stirred for a further 15 min. at −8° C
9. filtrationThe product was filtered off
10. washwashed twice with 15 ml of water
11. customdried in vaccuo

ORD record

ord-aec1ee2be0a8485ba15c4cd514d0d343

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951824B2