6-nitro-3-(N-propionyl-N-n-propylamino)chroman → 6-amino-3-(N-propionyl-N-n-propylamino)chroman

Participants

Reaction Conditions

Reaction Steps

A solution of 6-nitro-3-(N-propionyl-N-n-propylamino)chroman (17) (700 mg, 2.40 mmol) in glacial acetic acid (50 ml) was treated with zinc dust (1.0 g). The mixture was stirred at 50° C. for 90 minutes. The solution was filtered and acetic acid evaporated at reduced pressure. The product was dissolved in CH2Cl2 and washed with 5%-aqueous Na2CO3. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated. The crude product was chromatographed on silica (60 g), with CH2Cl2CH3OH (19:1) as eluant, yielding 350 mg (56%) of 6-amino-3-(N-propionyl-N-n-propylamino)chroman (18) as an oil.

Provenance & Evidence