Hydrochloric Acid → HCID 178519764, compound

Participants

Reaction Conditions

Reaction Steps

A solution 2-((3,4-dichlorophenyl)amino)-8-(1,3-dioxolan-2-yl)-6-nitroquinazolin-4-ol (1.08 g) in tetrahydrofuran (35 mL) and dimethylsulfoxide (1 mL) was treated with 10% (v/v) hydrochloric acid (25 mL). The resulting mixture was stirred at 40° C. for 7 h, then was cooled to room temperature and stirred for 16 h. Evaporation of the tetrahydrofuran in vacuo provided a brown slurry, from which the product was isolated by filtration. The brown solids were washed with water (50 mL) and dried. The crude product was dissolved in tetrahydrofuran (3.75 mL), dried over MgSO4, filtered and evaporated to afford the title compound (1.0 g) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 10.57 (s, 1H), 8.72 (d, J=2.7 Hz, 1H), 8.54 (bd, J=2.1 Hz, 1H), 8.03 (bd, J=2.1 Hz, 1H), 7.56 (d, J=8.7 Hz, 1H), 7.49 (dd, J=2.1, 8.7 Hz, 1H). HPLC Method A: 7.73 min. MS (APCI−): m/z 377, 379.

Provenance & Evidence