Hydrochloric Acid → 3-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

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Reaction Steps

To a stirred solution of 4,4,6-Trimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline (10 g) in Ethanol/water (150 mL/30 mL) was added concentrated hydrochloric acid (2 mL) and Iron Powder (20 g, 356 mmol). The resultant mixture was heated to reflux for 2 h. Iron Powder was filtered, and washed with ethanol. The combined filtrate was concentrated, and diluted with water. The mixture was extracted with ethyl acetate (250 mL×3). The combined organic layers were washed with saturated brine, and the brine was extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate, concentrated. The residue was treated with ether and hexane to afford 4.5 g of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine as brown solid (Yield: 50%).

Provenance & Evidence