4-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene → 5-Chloro-4-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-methylaniline

Participants

Reaction Steps

To a solution of 45.0 g of 4-chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene in 1200 ml of toluene was added 4.5 g of 5% platinum on carbon catalyst. This mixture was then changed to a 2 L stirred Parr pressure reactor. The reactor was flushed twice with nitrogen, then twice with hydrogen and then finally filled with hydrogen to a pressure of 250 psig. The internal pressure was maintained between 200 psig and 250 psig while the internal temperature was maintained between 40° and 45° C. during the course of the reaction. When hydrogen uptake ceased, the reaction mixture was removed from the reactor and filtered through celite. Removal of the toluene in vacuo afforded a yellow oil which slowly solidified. Recrystallization from a hexane-ethyl acetate mixture afforded 39.14 g of the desired aniline as white crystals. mp=180° C. NMR (CDCl3): 1.6-1.9 (m, 4H), 2.05 (s, 3H), 2.5-2.7 (m, 4H), 3.47 (broad s, 2H), 6.33 (d, J=8 Hz, 1H), 6.63 (s, 2H), 7.03 (d, J=8 Hz, 1H).

Provenance & Evidence