Malonic Acid → 2-Hydroxyquinoline

Participants

Reaction Conditions

Reaction Steps

To 2-bromo-3-aminoanisole 2B4 (378 mg, 1.87 mmol, 1 eq) and malonic acid (194 mg, 1.87 mmol) was added phosphorous oxychloride (175 μL, 1.87 mmol). The reaction was placed in a pre-heated bath (95° C.) and stirred for 30 minutes. The mixture was cooled, and diluted with ice water and stirred ca. 2 h to afford a grey solid. This was filtered and washed with water until free of acid and then taken up into 1N NaOH. Insoluble material was removed by filtration and the resulting aqueous solution was treated with EtOH (8 mL) before adjusting the pH to 5-6 with 1N HCl (aq). The desired product was filtered and dried to afford quinolone 3J1 (0.12 g, 24%) as a yellow solid. MS: 270.0 (M+H)+ and 291.9 (M+Na)+.

Provenance & Evidence