Sodium Carbonate → 6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine

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Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride (11.5 g, 0.033 mol), idopropane (21 g, 0.12 mol) and anhydrous sodium carbonate (20 g, 0.19 mol) in dimethylformamide (100 mL) was stirred at 100° C. for 5 hours. The solution was then evaporated, partitioned between ethyl acetate and water, and the ethyl acetate was evaporated to give a red oil. This was chromatographed on silica gel to give 8.2 g of 6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine. The product was crystallized from ethyl acetate:hexane to give 7.6 g of product, mp 79°-81° C. Anal. Calcd. for C15H22BrN3O2 : C, 50.57; H, 6.23; Br, 22.43; N, 11.79. Found: C, 50.59; H, 6.27; Br, 22.53; N, 11.69.

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