4-Nitrophenyl Acetate → HCID 21996530, compound

Participants

Reaction Steps

To a solution of 1-(2-aminoethyl)-7-formylamino1,2,3,4-tetrahydronaphthalene (1.80 g, 8.25 mmol) in THF (20 ml) was added added, under ice-cooling, lithium aluminum hydride (0.63 g, 16.5 mmol). The mixture was heated for 4 hours under reflux under argon atmosphere. The reaction mixture was cooled with ice, to which was added water (0.9 ml), followed by further addition of ethyl acetate, anhydrous magnesium sulfate and celite, successively. The mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was dissolved in DMF (20 ml). To the solution was added 4-nitrophenyl acetate (1.33 g, 7.34 mmol), and the mixture was stirred for 20 minutes at room temperature. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (methanol/ethyl acetate, 97:3-96:5) to give 1.10 g (yield 54%) of the above-titled compound as an oily product.

Provenance & Evidence