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. Quenched the cooled reaction mixture 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 dissolved in diethyl ether and to this was added n-hexane until the solution was cloudy, within a few minutes a thick flocculent solid had formed, filtered off, washed with n-hexane and dried to give benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine (60.59 gm 92% yield).

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

ORD record

ord-c0751ee483a647fabb972c69268f864a

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372836B2