反应详情

N-Acetylethylenediamine (14.5 g) was dissolved in 250 ml of methylene chloride under argon, treated in succession with 250 g of molecular sieve 4 Å and a solution of 28.1 g of 1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthaleneacetaldehyde in 190 ml of methylene chloride and refluxed for 21 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 35.3 g of brown, amorphous material, was chromatographed on 600 g of silica gel with ethyl acetate as the eluent. There were obtained 29.6 g (81%) of N-[2-(4,5-dihydro-8-methoxy-1H-benzo[g]indol-1-yl)-ethyl]acetamide which was processed without further purification.

1. additiontreated in succession with 250 g of molecular sieve 4 Å
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered over a Celite® pad
4. customThe crude product, 35.3 g of brown, amorphous material, was chromatographed on 600 g of silica gel with ethyl acetate as the eluent