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A Concise Synthesis of 2‐Amino‐1,2,3,4‐tetrahydronaphthalene‐6,7‐diol (‘6,7‐ADTN’) from Naphthalene‐2,3‐diol
Authors:Süleyman Gksu  Cavit Kazaz  Yaar Sütbeyaz  Hasan Seen
Institution:Süleyman Göksu,Cavit Kazaz,Ya?ar Sütbeyaz,Hasan Seçen
Abstract:2‐Amino‐1,2,3,4‐tetrahydronaphthalene‐6,7‐diol ( 2 ; 6,7‐ADTN) was synthesized starting from naphthalene‐2,3‐diol in seven steps and with an overall yield of 44%. Methylation of naphthalene‐2,3‐diol with dimethyl sulfate, followed by Friedel? Crafts acylation with AcCl, gave 2‐acetyl‐6,7‐dimethoxynaphthalene. 2‐Acetyl‐6,7‐dimethoxynaphthalene was converted to 6,7‐dimethoxynaphthalene‐2‐carboxylic acid by a haloform reaction. Birch reduction of the carboxylic acid with 4 mol‐equiv. of Na in liquid ammonia afforded 1,2,3,4‐tetrahydro‐6,7‐dimethoxynaphthalene‐2‐carboxylic acid, from which 2 was obtained by a Curtius reaction, followed by hydrogenolysis and demethylation.
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