Hydrochloric Acid → Quinazoline-6-carboxylic acid

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[CH:9]2)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15][CH:14]=2)[CH:9]=[N:10][CH:11]=1

Participants

Procedure

To a solution of quinazoline-6-carboxylic acid ethyl ester (79 mg, 0.391 mmol) in ethanol (4 mL) was added an aqueous solution of 1N sodium hydroxide (4 mL), and the solution was stirred for 1 hour at room temperature. 1N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and the solution was evaporated in vacuo. Ethanol was added to the residue, and the organic layer was concentrated. The residue was dissolved in an ethyl acetate-tetrahydrofuran mixture solvent, dried over anhydrous magnesium sulfate, then, evaporated in vacuo, and quinazoline-6-carboxylic acid (15 mg, 0.086 mmol, 22%) was obtained. This was used in the next reaction without purification.