Hexane → Benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine

Temperature

100 °C

4-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-2-ol (61.7 gm 197 mmol) was added to phenylphosphonic dichloride (180 mL) and heated to 100° C. in an oil bath, under N2 overnight. The starting material dissolved on heating to give a light yellow solution. The mixture was then quenched on to ice water (600 gm of ice+100 mL water) to give a pale yellow solid. Filtered off and washed the solid well with water. The solid was dissolved in ethyl acetate (600 mL) and washed with aqueous sodium hydrogen carbonate solution (10% w/v) until there was no further effervescence and the pH of the aqueous washings were basic. The organic layer was dried over sodium sulphate, filtered and evaporated to give a dirty yellow solid. The solid was then dissolved in diethyl ether. To this was then added n-hexane until the solution was cloudy. Within a few minutes a thick flocculent solid had formed, which was then filtered off, washed with n-hexane and dried to give the title compound (60.59 gm 92% yield).

1. dissolutionThe starting material dissolved
2. temperatureon heating
3. customto give a light yellow solution
4. customThe mixture was then quenched on to ice water (600 gm of ice+100 mL water)
5. customto give a pale yellow solid
6. filtrationFiltered off
7. washwashed the solid well with water
8. dissolutionThe solid was dissolved in ethyl acetate (600 mL)
9. washwashed with aqueous sodium hydrogen carbonate solution (10% w/v) until there
10. dry with materialThe organic layer was dried over sodium sulphate
11. filtrationfiltered
12. customevaporated
13. customto give a dirty yellow solid
14. customWithin a few minutes a thick flocculent solid had formed
15. filtrationwhich was then filtered off
16. washwashed with n-hexane
17. customdried

ORD record

ord-0a255941459b4e429be1423017f56ee1

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691877B2