Methyl iodide → 8-Methoxy-2-Methylquinoline

Participants

Reaction Steps

A mixture of 8-hydroxyquinaldine (5.0 g) and tetrabutyl ammonium iodide (1.1 g) in tetrahydrofuran (9 ml) was treated at room temperature with sodium hydroxide (4.5 g) in water (45 ml). Methyl iodide (3.7 ml) was added and the reaction stirred overnight. The THF was removed in vacuo and the remaining solution partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous layer was re-extracted with ethyl acetate and the organic extracts combined. The organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and saturated aqueous sodium chloride (100 ml). The organic layer was dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo to yield the desired product as an off-white solid (5.85 g).

Provenance & Evidence