Ethanol → 1-[2-(Acetylamino)ethyl]-6-ethoxyindan

To a solution of 1-[2-(acetylamino)ethyl]-6-hydroxyindan (1.00 g, 4.56 mmol), ethanol (0.32 ml, 5.47 mmol) and triphenylphosphine (1.32 g, 5.02 mmol) in THF (20 ml) was added dropwise, under ice-cooling, diethyl azodicarboxylate (0.87 g, 5.02 mmol). The mixture was stirred for 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water, and the mixture was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography (ethyl acetate→ethyl acetate/methanol, 95:5) to give 1-[2-(acetylamino)ethyl]-6-ethoxyindan. To this compound was added hydrazine hydrate (20 ml). The mixture was heated under reflux for 15 hours under argon atmosphere. The reaction mixture was cooled, to which was added water. The mixture was subjected to extraction with ethyl acetate. The extract solution was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 0.34 g (yield 36%) of the above-titled compound as an oily product.

1. temperaturecooling
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionTo the concentrate was added water
4. extractionthe mixture was subjected to extraction with ethyl acetate
5. washThe extract solution was washed with brine, which
6. dry with materialwas dried over anhydrous magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-48c5fedd133046a289a61671ded1bb8c

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235789B1