1,1,4,4-Tetramethyl-6-nitro-1,2,3,4-tetrahydronaphthalene → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Participants

Reaction Steps

To a solution of 2-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (79.0 g, 0.339 mol) in dichloromethane as added 1 g of 10% palladium on carbon and the mixture was hydrogenated at 40–50 psi of hydrogen for 20 hrs. The catalyst was removed by filtration and the organic and the aqueous layers were separated. The aqueous layer was made alkaline by addition of 1N NaOH and extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and evaporated to give 2-amino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene as a red-orange solid which was used in the next step without further purification.

Provenance & Evidence