Sulfuric Acid → 5,6-dimethoxy-2,3-dihydro-1H-inden-2-amine

Participants

Reaction Steps

A solution of 5,6-dimethoxy-2-hydroxyimino-1-indanone (0.27 moles, 6 g) in glacial acetic acid (500 ml) is added with 96% sulfuric acid (3.3 ml) and 10% Pd/C (1.5 g). The mixture is hydrogenated in a Parr apparatus (r.t., 35 psi). When the hydrogen absorption ceases, the catalyst is filtered off through celite, washing with methanol (70 ml). The solution is evaporated to dryness, to obtain a white solid which is dissolved in water, then extracted with ethyl acetate (2×70 ml). The aqueous solution is alkalinized with a 1M sodium hydroxide solution to pH=8-8.5. The product is extracted with methylene chloride (2×70 ml). The organic solution is dried over sodium sulfate and evaporated under vacuum to obtain the solid product. Yield: 4.6 g (88.5%)

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