2,5-Dimethoxybenzonitrile → 2,5-Dimethoxybenzenemethanamine

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Reaction Steps

A sample of 3.12 g of 2-cyano-1,4-dimethoxybenzene was reduced by 1 g of lithium aluminum hydride in 20 mL of THF at 0° C. to yield 3 g of 2-aminomethyl-1,4-dimethoxybenzene. This was then refluxed in a 1:1 (v/v) mixture of acetic acid and 48% aqueous hydrobromic acid overnight. The volatile components were removed under reduced pressure, and the crude 2-aminomethyl-1,4-hydroquinone HBr salt was used “as is” without further purification. Triethylamine (0.4 mL) was added to a mixture of 50 mg of compound (1) and 0.6 mmole of 2-aminomethyl-1,4-dihydroquinone HBr salt in 2 mL of dichloroethane, and stirred overnight. The crude dihydroquinone was then oxidized to the desired quinone compound (11) with ceric ammonium nitrate in a water/acetonitrile mixture.

Provenance & Evidence