N-isopropyl-6-nitro-1,2,3,4-tetrahydrocarbazole → N-isopropyl-6-amino-1,2,3,4-tetrahydrocarbazole

Participants

Reaction Conditions

Reaction Steps

The N-isopropyl-6-nitro-1,2,3,4-tetrahydrocarbazole (2.60 g) was dissolved in 100 mL of acetic acid, and the solution was added with 2.75 g of iron powder, warmed to 50° C. and stirred for 3 hours. The reaction mixture was filtered, and the filtrate was diluted by addition of water. The reaction mixture was made basic with 1 N sodium hydroxide solution, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: dichloromethane/ethyl acetate=7/3) to obtain 1.35 g of N-isopropyl-6-amino-1,2,3,4-tetrahydrocarbazole.

Provenance & Evidence