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Notizen zur Synthese sulfonierter Derivative von 5,6,7,8-Tetrahydro-1-naphthylamin und 5,6,7,8-Tetrahydro-2-naphthylamin
Courtin, Alfred
, p. 572 - 578 (2007/10/02)
Sulfonation of 5,6,7,8-tetrahydro-1-naphthylamine (1) with sulfuric acid gave a mixture of 1-amino-5,6,7,8-tetrahydronaphthalene-2-sulfonic acis (2), 4-amino-5,6,7,8-tetrahydronaphthalene-2-sulfonic acid (13) and 4-amino-5,6,7,8-tetrahydronaphthalene-1-sulfonic acid (3).The same reaction with 5,6,7,8-tetrahydronaphthylamine (20) yielded 3-amino-5,6,7,8-tetrahydronaphthalene-2-sulfonic acid (21); formation of 2-amino-5,6,7,8-tetrahydonaphthalene-1-sulfonic acid (16) or of 3-amino-5,6,7,8-tetrahydronaphthalene-1-sulfonic acid (24) was not observed.Treatment of 4-bromo-5,6,7,8-tetrahydro-1-naphthylamine (4) or of its 4-chloro analogue 5 with amidosulfuric acid gave 1-amino-4-bromo-5,6,7,8-tetrahydronaphthalenesulfonic acid (9) and its 4-chloro analogue 10, respectively, which were dehalogenated to 2.Preparations of 13 and 24 were achieved by sulfonation of 5-nitro-1,2,3,4-tetrahydronaphthalene (14) and 6-nitro-1,2,3,4-tetrahydronaphthalene (22) to 4-nitro-5,6,7,8-tetrahydronaphthalene-2-sulfonic acid (15) and 3-nitro-5,6,7,8-tetrahydronaphthalene-1-sulfonic acid (23), respectively, followed by Bechamp reductions.The sulfonic acid 13 was also obtained by hydrogenolysis of 4-amino-1-bromo-5,6,7,8-tetrahydronaphthalene-2-sulfonic acid (11) or of its 1-chloro analogue 12; compounds 11 and 12 were synthesized from N-(4-bromo-5,6,7,8-tetrahydro-1-naphthyl)acetamide (7) and from its 4-chloro analogue 8, respectively, by sulfonation with oleum and subsequent hydolysis.By 'baking' the hydrogensulfate salt of 1 or 20 compounds 3 and 21 were obtained, respectively.Synthesis of 16 was achieved by sulfur dioxide treatment of the diazonium chloride derived from 2-nitro-5,6,7,8-tetrahydro-1-naphthylamine (17) giving 2-nitro-5,6,7,8-tetrahydronaphthalene-1-sulfonyl chloride (18), followed by hydrolysis of 18 to the corresponding sulfonic acid 19 and final reduction.
