Hydroxide → HCID 22040275, compound

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 2-amino-4-chlorophenol (2.56 g, 17.83 mmol) in tetrahydrofuran (40 mL) was added a solution of hydroxide (0.72 g, 18 mmol) in water (15 mL). The mixture was stirred at 0° C. for 5 min. A solution of methyl azeloyl chloride (3.9 g, 17.67 mmol) in tetrohydrofuran (10 mL) was added dropwise to this mixture. The resulting mixture was stirred at 0° C., then gradually warmed to room temperature, and stirred at room temperature overnight. A solution of sodium hydroxide (2N, 25 mL) was added to the reaction mixture. The mixture was stirred at room temperature and monitored by TLC. When the starting material was no longer visible, the reaction mixture was concentrated in vacuo. The residue was acidified to pH 2, and the precipitated solid was collected by filtration. This crude product was dissolved in methanol (50 mL), decolorized with activated charcoal, and filtered. A small amount of acetone and water was added to the filtrate, and the mixture refrigerated overnight. A solid was formed, collected by filtration, washed with water, and dried to give the product as a pale yellow, crystalline solid (3.0 g, 54%); mp 117°-118° C.; 1H NMR (DMSO-d6) δ7.96 (d. J=2.5 Hz, 1H), 6.95 (dd, J=8.6, 2.6 Hz, 1H), 6.85 Hz, 1H), 2.39 (t, J=7.3 Hz, 2H), 2.19 (t, J=7.3 Hz, 2H), 1.40-1,61 (m, 4H), 1.20-1.35 (m, 6H). Anal. Calcd for C5H20CINO4 :C, 57.42; H, 6.42; N, 4.46. Found: C, 57.24; H, 6.30; N, 4.41.

Provenance & Evidence