Water → HCID 89494760, compound

Participants

Reaction Steps

After DMF (13.30 mL, 172.6 mmol) was cooled to 0° C. and POCl3 (2.68 mL, 28.79 mmol) was added dropwise thereto, the mixture was stirred for 20 minutes, warmed to room temperature, and then stirred for 1 hour. To this reactant, a solution in which the 3-(isopropyl(prop-2-ynyl)amino)phenol compound of Chemical Formula 3 (2.18 g, 11.51 mmol) was dissolved in DMF (10 mL) was added, and then the mixture was stirred for 12 hours. Distilled water (30 mL) was added to the post-reaction mixture, and the result was neutralized to between pH 7 and 8 by adding sodium bicarbonate solid. After this mixture was partitioned to acetic acid (100 mL) and distilled water (30 mL), the organic layer was separated, washed with saturated salted water (10 mL), dried with anhydrous sodium sulfate, filtered and vacuum distilled, and the residue obtained was column chromatographed on silica gel (hexane/ethyl acetate (7:1)) to give 2-hydroxy-4-(isopropyl(prop-2-ynyl)amino)benzaldehyde (2.05 g, 82%). 1H NMR (500 MHz, CDCl3) d 11.52 (s, 1H), 9.55 (s, 1H), 7.33 (d, 1H, J=8.7 Hz), 6.46 (dd, 1H, J=2.3, 8.7 Hz), 6.29 (d, 1H, J=2.3 Hz), 4.19-4.22 (m, 1H), 3.98 (d, 2H, J=2.7 Hz), 2.23 (t, 1H, J=2.7 Hz), 1.29 (d, 6H, J=6.9 Hz); 13C NMR (125 MHz, CDCl3) d 192.7, 164.2, 154.7, 135.3, 112.4, 105.4, 98.5, 80.4, 72.0, 49.1, 33.3, 20.2 (2).

Provenance & Evidence