Hydrochloric Acid → 1H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dione

Participants

Reaction Conditions

Reaction Steps

2-Hydroxyimino-N-(6-quinolinyl)acetamide (7.00 g, 32.5 mmol) was combined with 70 mL of concentrated sulfuric acid with stirring and heated to a reaction temperature of 120° C. for 20 min, followed by an hour at 95° C. The reaction was allowed to cool to room temperature and was added dropwise to a mixture of 155 g (1.25 mole) of sodium carbonate monohydrate and 200 g of ice. After the addition was complete, water (600 mL) was added gradually to the mixture with stirring until all inorganic white solid was dissolved. The aqueous mixture was neutralized to pH 7 with 1 M hydrochloric acid and the product was collected by filtration. The collected solid was added to 200 mL of water and dissolved by dropwise addition of 1 M hydrochloric acid to free entrapped salts. The product was then precipitated by addition of saturated aqueous sodium bicarbonate to pH 7. The product was collected by filtration and dried under vacuum at 55° C. to give 3.89 g (60%) of 3-H-pyrrolo[3,2-f]quinoline-1,2-dione as a red-brown solid. Mass spectrum (negative ion chemical ionization): m/z=197 (30%). NMR (DMSO-d6): δ7.43 (d, 1H, J=8.8 Hz), 7.66 (dd, 1H, J=4.1, 8.4 Hz); 8.29 (d, 1H, J=8.8 Hz); 8.72 (d, 1H, J=8.4 Hz); 8.82 (d, 1H, J=3.3 Hz); 11.2 (s, 1H).

Provenance & Evidence