Iodine → 3-Ethyl-8-methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

Freshly distilled 2-ethyl acrolein (1.7 ml) was added, over 20 minutes, to a solution of o-anisidine (1.5 g) and iodine (20 mg) in 70% sulphuric acid (10 ml) stirring at 110° C. After 2 hours the reaction was cooled to 0° C. and basified with 25% aqueous sodium hydroxide (pH 13). The aqueous layer was extracted with ethyl acetate (2×100 ml) and the extracts combined. The organic layer was extracted with 2M hydrochloric acid (2×100 ml) and the combined acidic extracts basified once again with 25% sodium hydroxide. The aqueous layer was extracted with ethyl acetate (2×100 ml), the extracts combined, dried over magnesium sulphate, filtered, and the filtrate evaporated in vacuo. The residue was purified by column chromatography, eluting with 25%-50% ethyl acetate in hexane, to yield the title product as a tan oil (0.42 g).

Provenance & Evidence