Iodoethane → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Participants

Reaction Steps

To a solution of step-a product (30 g, 0.118 mol) in acetonitrile (240 ml, 8 times), cesium carbonate (71.7 g, 0.22 mol, 1.9 eq) was added and stirred for some time. Ethyl iodide (19.8 g (10.19 ml), 0.12 mol, 1.1 eq) was added and the overall reaction mixture was stirred for 1 hr at rt. Progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.6). On completion of the reaction, filtered the contents, washed with acetonitrile (2×50 ml) and distilled off the solvent. Residue obtained was diluted with ethyl acetate (200 ml) and washed with water 92×100 ml). Dried the contents over sodium sulfate and distilled off the solvent completely. The crude obtained was taken in diisopropyl ether (100 ml), stirred for 10-15 min and filtered. Solid obtained was washed with diisopropyl ether again and dried to yield the required product as an off white solid (23 g, 69% yield).

Provenance & Evidence