Hydrochloric Acid → HCID 59334582, compound

Participants

Reaction Steps

To a solution of methyl 3-amino-4-chloro-2-methylbenzoate (6.50 g, 32.6 mmol) and ammonium tetrafluoroborate (4.44 g, 42.3 mmol) in water (2.0 mL) and concentrated hydrochloric acid (17.6 mL, 212 mmol) was added a solution of sodium nitrite (2.25 g, 32.6 mmol) in water (8 mL) at 0° C. for 25 min, and the mixture was stirred for 35 min. The precipitated solid was collected by filtration, washed with ether, and dried under reduced pressure. The obtained solid was dissolved in chloroform (100 mL), and 18-crown-6 (258 mg, 0.98 mmol) and potassium acetate (3.52 g, 35.8 mmol) were added. The reaction mixture was stirred at room temperature for 2 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was triturated with hexane, and collected by filtration to give the title compound (16.1 g, yield 50%). 1H-NMR (CDCl3) δ: 4.03 (3H, s), 7.45 (1H, d, J=7.6 Hz), 7.90 (1H, d, J=7.6 Hz), 8.64 (1H, s), 10.71 (1H, br s).

Provenance & Evidence