Hydrochloric Acid → HCID 24971987, compound

Participants

Reaction Steps

A suspension of 2 ethyl-6-nitroaniline (Example 139d) (1.96 g, 11.80 mmol) in a solution of HCl (3.0M, 24.5 mL) was stirred at room temperature for 20 min. After cooling to 0-5° C., a solution of NaNO2 (1.63 g, 23.6 mmol) in water (12.25 mL) was added over a period of 10 min. The obtained mixture was stirred at 0-5° C. for 30 min, and the obtained homogeneous solution was transferred to a solution of CuCN (2.63 g, 29.5 mmol) and KCN (5.06 g, 77.8 mmol) in water (60 mL) and EtOH (31.0 mL). The resulting mixture was stirred vigorously at room temperature for 30 min, and then heated at 70° C. for another 30 min to complete the reaction. The cold mixture was filtered and extracted with EtOAc (3×100 mL). The combined extract was washed with NaOH (0.5M) and brine, and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel eluting with 30% EtOAc in hexanes, to afford 0.66 g (33%) of the title compound as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 8.18-8.24 (m, 1H), 7.85-7.97 (m, 2H), 2.93 (q, J=7.2 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H).

Provenance & Evidence