Tetralinsulfonsäuren und ihre Derivate. I. Bereitung der Nitrotetralinsulfonsäuren und ihrer Sulfochloride

Kloubek, J.; Šíp, Josef; Ettel, Viktor

doi:10.1002/prac.19630220108

J. Prakt. Chem.

1963

DOI: 10.1002/prac.19630220108

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Tetralinsulfonsäuren und ihre Derivate. I. Bereitung der Nitrotetralinsulfonsäuren und ihrer Sulfochloride

J. Kloubek¹,

Josef Šíp²,

Viktor Ettel³

Abstract: Inh altsiibersichtEs wurden die 7-Nitro-l,2,3,4-tetrahydronaphthalin-5-und 8-Nitro-l,2,3,4-tetrahydronaphthalin-6-sulfonsiiuren und ihre Chloride hergestellt.

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1981

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Notizen zur Synthese sulfonierter Derivate von 5,6,7,8‐Tetrahydro‐1‐naphthylamin und 5,6,7,8‐Tetrahydro‐2‐naphthylamin

Courtin

1981

Helvetica Chimica Acta

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SummarySulfonation of 5,6,7,8-tetrahydro-1-naphthylamine (1) with sulfuric acid gave a mixture of l-amino-5,6,7,8-tetrahydronaphthalene-2-sulfonic acid (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-tetrahydro-2-naphthylamine (20) yielded 3-amino-5,6,7,8-tetrahydronaphthalene-2-sulfonic acid (21); formation of 2-amino-5,6,7,8-tetrahydronaphthalene-1-sulfonic acid (16) or of 3-amino-5,6,7,8-tetrahydronaphthalene-l-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 l-amino-4-bromo-5,6,7,8-tetrahydronaphthalene-2-sulfonic 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-l.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-I-sulfonic acid (23), respectively, followed by B6champ reductions. The sulfonic acid 13 was also obtained by hydrogenolysis of 4-amino-l-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-l-naphthyl)acetamide (7) and from its 4-chloro analogue 8, respectively, by sulfonation with oleum and subsequent hydrolysis. 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.

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Notizen zur Synthese sulfonierter Derivate von 5,6,7,8‐Tetrahydro‐1‐naphthylamin und 5,6,7,8‐Tetrahydro‐2‐naphthylamin

Courtin

1981

Helvetica Chimica Acta

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Tetralinsulfonsäuren und ihre Derivate. I. Bereitung der Nitrotetralinsulfonsäuren und ihrer Sulfochloride

Abstract: Inh altsiibersichtEs wurden die 7-Nitro-l,2,3,4-tetrahydronaphthalin-5-und 8-Nitro-l,2,3,4-tetrahydronaphthalin-6-sulfonsiiuren und ihre Chloride hergestellt.

Cited by 1 publication

References 7 publications

Notizen zur Synthese sulfonierter Derivate von 5,6,7,8‐Tetrahydro‐1‐naphthylamin und 5,6,7,8‐Tetrahydro‐2‐naphthylamin

Notizen zur Synthese sulfonierter Derivate von 5,6,7,8‐Tetrahydro‐1‐naphthylamin und 5,6,7,8‐Tetrahydro‐2‐naphthylamin

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