Nitric Acid → 6-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one

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Reaction Conditions

Reaction Steps

A procedure for the synthesis of mono-amino substituted tetralone from tetrahydronaphthalene is illustrated with an exemplary synthetic route in FIG. 4. To an ice-cold, stirred solution of 6-methoxy-1-tetralone (20, 17.6 g, 0.10 mol) in acetone (30 mL) was added dropwise a mixture of sulfuric acid (18 mL, 96.0%) and nitric acid (15 mL, 68.0–70.0%). After the addition was complete, the reaction was stirred at 0° C. for 6 hours, and TLC was employed to monitor the reaction progress. The reaction mixture was poured into ice-water, and the mixture was partitioned between CH2Cl2 (3×200 mL) and water (200 mL). The organic layer was washed by saturated NaHCO3 solution and water (200 mL each), dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 6-Methoxy-5-nitro-1-tetralone (21, 7.74 g, 0.035 mol) and 6-methoxy-7-nitro-1-tetralone (22, 6.63 g, 0.030 mol) were obtained after purification by column chromatography:

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