Ammonium Chloride → 7-Amino-1,2,3,4-tetrahydronaphthalen-1-one

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Reaction Conditions

Reaction Steps

A solution of 7-nitro-3,4-dihydro-1(2H)-naphthalenone (10.0 g, 52.3 mmol) in ethanol/water (4:1 mixture, 200 mL) was treated with iron (10.3 g), and ammonium chloride (1.1 g), stirred at 85° C. for 4 hours, and filtered. The filtrate was concentrated and the concentrate was dissolved in 400 mL of ethyl acetate, washed with brine (5×), dried (Na2SO4), filtered, and concentrated. The concentrate was treated with diethyl ether and filtered. The filter cake was washed with diethyl ether and dried under vacuum to provide 7.56 g of the desired product. The filtrate was concentrated to provide 0.39 g of additional product. MS (DCI) m/e 162 (M+H)+, 179 (M+NH4)+.

Provenance & Evidence