Electronic Resource
New York, NY
:
Wiley-Blackwell
Helvetica Chimica Acta
60 (1977), S. 19-26
ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthese of sulfonated derivatives of 2-amino-p-xyleneSulfonation 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19770600104
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