6-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one → 1-Hydroxy-6-methoxy-5-nitro-1-(3',4',5'-trimethoxyphenyl)tetralin

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Reaction Steps

6-Methoxy-5-nitro-1-tetralone (21) (2.65 g, 12.0 mol) was added at −20° C. to the trimethoxyphenyllithium and stirring was continued for 2 h (−20° C. -RT). The mixture was partitioned between CH2Cl2 and water, the organic layer was dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo, to afford 1-Hydroxy-6-methoxy-5-nitro-1-(3′,4′,5′-trimethoxyphenyl)tetralin (30) as a crude yellow oil. (GC-MS shows the yield is about 55%). This compound, without purification, was added to a refluxing mixture of acetic acid (10 mL) and water (80 mL), and iron (0.5 g) was added. After heating at reflux for 1 h, the mixture was partitioned between CH2Cl2 (3×100 mL) and water (100 mL). The organic layer was washed with NaHCO3 (sat.) and water (100 mL each), dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. Purification by column chromatography afforded 5-Amino-6-methoxy-1-(3′,4′,5′-trimethoxyphenyl)-3,4-dihydronaphthalene (31):

Provenance & Evidence