Ethanol → HCID 178486927, compound

Participants

Reaction Conditions

Reaction Steps

A 1 L flask was charged with 4-amino-6-bromo-7-methoxycinnoline-3-carboxamide (Method 15) (30 g, 101 mmol) and ethanol (650 ml). A suspension of potassium hydroxide (100 g, 1782 mmol) in water (350 ml) was added to the reaction and the mixture was stirred at reflux for 9 days. The reaction was then cooled and filtered through a pad of Celite which was washed with water (˜250 mL). The resulting filtrate was conc. in vacuo to remove the ethanol and the resulting aqueous solution was acidified with conc. HCl to pH 3. A precipitate formed which was collected by vacuum filtration. The resulting solid was suspended in 1.4 L of ethanol, heated to 75° C. for 15 minutes, and cooled to room temperature which provided the crude precipitate which was collected by vacuum filtration. The filter cake was washed with ethanol (˜200 mL) and diethyl ether (˜200 mL) to yield the title compound as a brown solid which was used without further purification (26.0 g, 86%). 1HNMR: 14.60 (m, br, 2H), 8.35 (s, 1H), 7.23 (s, 1H), 4.08 (s, 3H); m/z: 310.

Provenance & Evidence