Hydrochloric Acid → HCID 13012490, compound

Participants

Reaction Steps

7-Nitro-1-tetralone (8.32 g, 0.044 mol) and concentrated hydrochloric acid (24 ml, 0.29 mol) were dissolved in methanol (100 ml), and an iron powder (7.30 g, 0.13 mol) was gradually added over 1 hour. After stirring for 1 hour, the reaction mixture was concentrated. 4N Sodium hydroxide solution and ethyl acetate were added to the residue, and extraction was conducted. The organic layer was dried, and concentrated. Tetrahydrofuran (100 ml) and triethylamine (5.05 g, 0.05 mol) was added to the residue. Further, acetyl chloride (3.92 g, 0.05 mol) was added under ice-cooling. After stirring for 30 minutes, ethyl acetate and 1N hydrochloric acid were added, and extraction was conducted. The organic layer was concentrated, and the residue was purified with silica gel column chromatography (development solvent: ethyl acetate), to give 7-acetylamino-1-tetralone (7.52 g) as a white powder.

Provenance & Evidence