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A study was carried out to convert 1-tetralone and some of its derivatives to the amines by Leuckart reaction. In this reaction, the ketones (1) 1-cetralone, (2) 5-methoxy-1 -tetra1 one, (3) 6-methoxy-l-tetralone, (4) 7-methoxy-1-tetralone and (5) 5,7-dimethyl-l-tetralone were converted to the formyl derivatives. These formamides namely, (la) 1,2,3,4-tetrahydro-l-naphthvl, (2a) 5-methoxy-1, 2,3,4-tetrahydro-1-naphthy1, (3a) 6-methoxy1,2,3,4-tetrahydro-1-naphthy1, (4a) 7-methoxy-1,2,3, 4-tetrahydro-l-naphthyl and (5a) 5,7-dimethy11,2,3,4-tetrahvdro-l-n3phthyl formamides were then hydrolyzed to their corresponding amines:(lb) 1-aminotetralin , (2b) 1-amino-5-methoxytetra1in, (3b) 1-amino-G-methoxytetralin, (4) l-.omino-7-methoxytetralin, and (5b) l-amino-5,7-dimethyltetral This was carried out by both acidic (concentrated hydrochloric acid) and basic (1C% aqueous NaOH) conditions. The former gave yields ranging from 0% to 75%, while the latter gave yields ranging from 90% to 97%. Acid hydrolysis of 3a and 4a gave black-gummy compounds and no amines were obtained. This showed that hydrolysis of formyl derivatives under basic conditions gave better results and is recommended.

Application of tetralinylis as carboxamide protecting groups in peptide synthesis.