8-Bromo-3-nitrochroman → 8-Bromo-3,4-dihydro-2H-1-benzopyran-3-amine

Participants

Reaction Conditions

Reaction Steps

8-Bromo-3-nitrochroman (400 mg; 1.55 mmol) was dissolved in glacial acetic acid (30 ml) and zinc dust (2 g) was added. The mixture was heated to 100° C. for 15 minutes. The zinc dust was filtered off and washed with dichloromethane. The solvent was evaporated and the remaining oil extracted with diluted hydrochloric acid/dichloromethane. The phases were separated and the pH of the water layer was adjusted to 11 with 2N NaOH. The water layer was extracted with dichloro-methane. The phases were separated and the organic layer dried (Na2SO4). The solvent was evaporated yielding 214 mg (61%) of 8-bromo-3-aminochroman.

Provenance & Evidence