Hydrochloric Acid → HCID 59708701, compound

Participants

Reaction Steps

To a 100 mL recovery flask was added 3-aminophenoxyacetic acid 2 (2.00 g, 12.0 mmol, 1.0 eq.) and a stirbar. Acetic acid (5 mL), conc. HCl (2 mL) and H2O (3 mL) were added to the flask. The reaction mixture was cooled to 0° C. upon which a solution of NaNO2 (0.908 g, 13.2 mmol, 1.1 eq.) in H2O (3 mL) was added over a period of 20 sec. The mixture was stirred for 5 minutes. A solution of NaN3 (0.855 g, 13.2 mmol, 1.1 eq.) in H2O (3 mL) was added slowly to the reaction mixture upon which the mixture foamed. The reaction mixture was stirred at 0° C. for 30 min and at room temperature for an additional 1 h. A light brown solid precipitates out of solution. The suspension was filtered and washed with cold H2O to yield a light-brown solid (1.48 g). Upon drying, the more precipitate formed in the filtrate. The precipitate was refiltered to yield more product (0.17 g). Total yield: 1.65 g, 71%. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 192.1 (M−H)−1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 7.31-7.27 (t, 1H), 6.73-7.69 (m, 2H), 6.59-6.58 (m, 1H), 4.62 (s, 2H) ppm.

Provenance & Evidence