3-Cyanopyridine → HCID 178420778, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-cyanopyridine (1.1 g, 10.6 mmol) in DMF (15 mL) was added ammonium chloride (718 mg, 13.4 mmol) and sodium azide (824 mg, 12.7 mmol) and the resultant slurry was vigorously stirred at 90° C. for 15 h. The DMF was removed in vacuo, the residue was dissolved in aqueous potassium hydroxide (1 M, 20 mL), washed with EtOAc (2×25 mL), the aqueous layer was adjusted to pH ˜3 with aqueous HCl (6 N) and the solid was collected by filtration to afford the title compound 64 (904 mg, 46% yield) as a white solid: mp=239-241° C. dec.; 1H NMR (CDCl3) δ 9.21 (m, 1H), 8.76 (m, 1H), 8.39 (m, 1H), 7.64 (m, 1H); LRMS (ESI) m/z calcd for C6H6N5 [M+H]+ 148. found 148; HRMS (ESI) m/z calcd for C6H6N5 [M+H]+ 148.0623. found 148.0624; HPLC>99% (tR=4.88 min, 60 (A):40 (B): 0.009 (C); tR=3.74 min, 60 (A):40 (B): 0.02 (C)).

Provenance & Evidence