Hydrochloric Acid → HCID 178520493, compound

Participants

Reaction Conditions

Reaction Steps

3-[2-(3,4-Dichlorophenylamino)-4-hydroxy-6-nitro-quinazolin-8-yl]propionicacid. To a solution of 3-(2-chloro-4-hydroxy-6-nitroquinazolin-8-yl)propionic acid methyl ester (0.536 g) in 1-methyl-2-pyrrolidinone (10 mL) was added 3,4-dichloroaniline (0.890 g). The reaction mixture was heated to 125° C. for 6 h, then cooled to room temperature and stirred for 48 h. The solvent was removed in vacuo and the residue was diluted with water (20 mL). The precipitate that formed was collected via filtration, washed with water and dried to give a brown solid which was dissolved in tetrahydrofuran (30 mL) and water (30 mL). To this solution was added lithium hydroxide (0.507 g) and the resulting mixture was stirred at room temperature for 17 h. The pH of the solution was adjusted to ca. 3 using 1.2 M hydrochloric acid and the solvent was removed in vacuo. The residue was triturated with water and dried to afford the title compound as a solid (0.744 g). 1H NMR (300 MHz, DMSO-d6): 12.20 (s, 1H), 11.58 (s, 1H), 9.85 (s, 1H), 8.58 (d, J=2.8 Hz, 1H), 8.34 (d, J=2.8 Hz, 1H), 8.24 (D, J=2.8 Hz, 1H), 7.67-6.55 (m, 2H), 3.18 (t, J=7.5 Hz, 2H), 2.67 (t, J=7.3 Hz, 2H); HPLC (Method D): 7.68 min; MS (ES−): m/z 421.

Provenance & Evidence