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Zur Synthese sulfonierter Derivate von 4‐ und 5‐Aminoindan
Author(s) -
Courtin Alfred
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630817
Subject(s) - sulfonic acid , chemistry , hydrolysis , salt (chemistry) , chloride , acid hydrolysis , synthon , organic chemistry
On the Synthesis of Sulfonated Derivatives of 4‐ and 5‐Aminoindan Baking the hydrogensulfate salt of 4‐aminoindan (1) and 5‐aminoindan (2) led, respectively, to 4‐aminoindan‐7‐sulfonic acid (3) and 5‐aminoindan‐6‐sulfonic acid (4). Acid 4 was also obtained by direct sulfonation of 2. 4‐Aminoindan‐6‐sulfonic acid (5) and 6‐aminoindan‐4‐sulfonic acid (6) were prepared by sulfonation of 4‐nitroindan (7) and 5‐nitroindan (9) , respectively, to 4‐nitroindan‐6‐sulfonic acid (8) and 6‐nitroindan‐4‐sulfonic acid (10) , followed by a Béchamp ‐reduction. Treatment of 1 with amidosulfuric acid gave 3 , whereas the same reaction with 2 led to a mixture of 4 and 5‐aminoindan‐4‐sulfonic acid (11). Independent synthesis of 11 was achieved by the following sequence of reactions: sulfur dioxide treatment of the diazonium chloride derived from 4‐amino‐5‐nitrodan (13) gave 5‐nitroindan‐4‐sulfonyl chloride (14) ; hydrolysis to 5‐nitroindan‐4‐sulfonic acid (15) , and final reduction. The 4‐aminoindan‐5‐sulfonic acid (16) was synthesized by treatment of 4‐amino‐7‐bromoindan (18) with amidosulfuric acid to give 4‐amino‐7‐bromoindan‐5‐sulfonic acid (19) followed by hydrogenolysis. Sulfonation of 4‐acetyl‐amino‐7‐bromoindan (17) with oleum followed by hydrolysis led to 7‐amino‐4‐bromoindan‐5‐sulfonic acid (20) , the structure of which was confirmed by reductive dehalogenation to 5 .