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Zur Synthese sulfonierter Derivate von 2-Amino-p-xylol

✍ Scribed by Alfred Courtin; Hans-Rudolf von Tobel

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
582 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthese of sulfonated derivatives of 2‐amino‐p‐xylene

Sulfonation of 2‐amino‐p‐xylene (2) gave 2‐amino‐p‐xylene‐5‐sulfonic acid (1). The 2‐amino‐p‐xylene‐6‐sulfonic acid (3) was prepared via three routes: (1) sulfonation of 2‐amino‐5‐chloro‐p‐xylene (19) to 5‐amino‐2‐chloro‐p‐xylene‐3‐sulfonic acid (20) followed by hydrogenolysis; (2) sulfur dioxide treatment of the diazonium salt derived from 2‐amino‐6‐nitro‐p‐xylene (21) to 2‐nitro‐p‐xylene‐6‐sulfonyl chloride (11) followed by hydrolysis to 2‐nitro‐p‐xylene‐6‐sulfonic acid (4) and Béchamp reduction; (3) Béchamp reduction of 2‐chloro‐3‐nitro‐p‐xylene‐5‐sulfonic acid (13) to 3‐amino‐2‐chloro‐p‐xylene‐5‐sulfonic acid (16) and subsequent hydrogenolysis. Catalytic reduction of 13 in aqueous sodium carbonate solution gave mixtures of 3 and 16. 2‐Amino‐p‐xylene‐3‐sulfonic acid (27) was synthesized via two routes: (1) reaction of 19 with sulfamic acid to 2‐amino‐5‐chloro‐p‐xylene‐3‐sulfonic acid (26) followed by hydrogenolysis; (2) sulfur dioxide treatment of the diazonium salt derived from 2‐amino‐3‐nitro‐p‐xylene (28) to 2‐nitro‐p‐xylene‐3‐sulfonyl chloride (12), hydrolysis to 2‐nitro‐p‐xylene‐3‐sulfonic acid (7) and Béchamp reduction.

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