Hydrochloric Acid → HCID 10468897, compound

Participants

Reaction Conditions

Reaction Steps

A 3-L flask equipped with a thermometer and mechanical stirrer was charged with concentrated hydrochloric acid (140 mL), 1N hydrochloric acid (380 mL) and absolute ethanol (1.10L) and cooled to 5° C. in an ice bath. 3-Amino-2-chloro-4-[(2,6-difluorobenzyl) amino]pyridine(40 g, 0.15mol)(from example 1B) was added followed by the addition of sodium nitrite(13.3 g, 0.19 mol). The solution was stirred for 35 minutes at 5° C., ammonium hydroxide was added to pH9, and the solution extracted with chloroform (2×1.00L). The combined organic extracts were dried (sodium sulphate) and concentrated to produce 4-chloro-1-(2,6-difluorobenzyl)-1H-1,2,3- triazolo[4,5-c]pyridine as a damp pink solid in quantitative yield, sufficiently pure for further reaction. A sample was purified by flash column chromatography to give the analytical sample, mp.=133°-139° C. 1H NMR (DMSO-d6): 6.10 (s, 2H, CH2), 7.10-7.65(m, 3H, C-3'H, C-4'H, C-5'H), 7.95 (d, J=5.9 Hz, 1H, C-7H), 8.43 (d, J=5.9 Hz, 1H, C-6H).

Provenance & Evidence