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Ronald T. Coutts and Jerry L. Malicky. 
“The Synthesis of Analogs of the Hallucinogen 1-2,5-Dimethoxy-4-methylpheny1-2-aminopropane DOM. 11.' Some Ring-methoxylated 1-Amino-and 2-Aminoindanes”. 
Can. J. Chem.. 1973 Mar. 15;52(381):381-9.
The synthesis of 2-amino-4,7-dimethoxy-5-methylindane 12~1t,h e cyclic analog of the known hallucinogen 1-2,5-dimethoxy-4-methylpheny1-2-aminopropae DOM, is described. The key intermediate was trans-2-amino-4,7-dimethoxy-6-methyl-l-indanol trans-IOa which was converted to 12a in two ways. The prolonged action of hydrochloric acid on trans-lOa gave 4,7-dimethoxy-5-methyl-2-indanone Ild, the oxime of which, on catalytic reduction, was converted to 12a in low yield. A direct catalytic reduction of trans-l0a in the presence of hydrochloric acid also gave l2a, together with cis-2-amino-4,7-dimethoxy-6-methyl-I-indanol cis-lOa. The synthesis and properties of other derivatives of 2-aminoindane, and some derivatives of l-amino-indane are also described.
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