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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

✍ Scribed by Süleyman Göksu; Cavit Kazaz; Yaşar Sütbeyaz; Hasan Seçen

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
69 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

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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