𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Zur Synthese sulfonierter Derivate von 4- und 5-Aminoindan

✍ Scribed by Alfred Courtin

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
496 KB
Volume
63
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

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.

📜 SIMILAR VOLUMES

Zur Synthese sulfonierter Derivate von 4
Zur Synthese sulfonierter Derivate von 4-Fluoranilin
✍ Alfred Courtin 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 339 KB

**Syntheses of Sulfonated Derivatives of 4‐Fluoroaniline** Synthesis of 2‐amino‐5‐fluorobenzenesulfonic acid (**2**) was achieved by baking the hydrogen sulfate of 4‐fluoroaniline (**1**). Sulfonation of __p__‐fluoroacetanilide (**4**) with oleum followed by hydrolysis gave 5‐amino‐2‐fluorobenzenes

Zur Synthese sulfonierter Derivate von 2
Zur Synthese sulfonierter Derivate von 2-Fluoranilin
✍ Alfred Courtin 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 521 KB

Syntheses of Sulfonated Derivatives of 2‐Fluoroaniline Synthesis of 4‐amino‐3‐fluorobenzenesulfonic acid (**3**) was achieved in two ways: reaction of 2‐fluoroaniline (**1**) with amidosulfonic acid and by first conventionally converting 4‐nitro‐3‐fluoroaniline (**8**) to 4‐nitro‐3‐fluorobenzenesul

Zur Synthese sulfonierter Derivate von 2
Zur Synthese sulfonierter Derivate von 2,3-Dimethylanilin und 3,4-Dimethylanilin
✍ Alfred Courtin; Hans-Rudolf Von Tobel 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 711 KB

**On the Synthesis of Sulfonated Derivatives of 2,3‐Dimethylaniline and 3,4‐Dimethylaniline** Baking the hydrogensulfate salt of 2,3‐dimethylaniline (**1**) or of 3,4‐dimethylaniline (**2**) led to 4‐amino‐2,3‐dimethylbenzenesulfonic acid (**4**) and 2‐amino‐4,5‐dimethylbenzenesulfonic acid (**5**)

Zur Synthese sulfonierter Derivate von 2
Zur Synthese sulfonierter Derivate von 2-Amino-p-xylol
✍ Alfred Courtin; Hans-Rudolf von Tobel 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 German ⚖ 582 KB

**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)**

Zur Synthese sulfonierter Derivate von 4
Zur Synthese sulfonierter Derivate von 4-Amino-1,3-dimethylbenzol und 2-Amino-1,3-dimethylbenzol
✍ Alfred Courtin; Hans-Rudolf Von Tobel; Paul Doswald 📂 Article 📅 1978 🏛 John Wiley and Sons 🌐 German ⚖ 571 KB

**Syntheses of Sulfonated Derivatives of 4‐Amino‐1, 3‐dimethylbenzene and 2‐Amino‐1, 3‐dimethylbenzene** Direct sulfonation of 4‐amino‐1, 3‐dimethylbenzene **(1)** and sulfonation of 4‐nitro‐1,3‐dimethylbenzene (**4**) to 4‐nitro‐1,3‐dimethylbenzene‐6‐sulfonic acid (**3**) followed by reduction yie

Notizen zur Synthese sulfonierter Deriva
Notizen zur Synthese sulfonierter Derivate von 5,6,7,8-Tetrahydro-1-naphthylamin und 5,6,7,8-Tetrahydro-2-naphthylamin
✍ Alfred Courtin 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 499 KB

**Notes on the Synthesis of Sulfonated Derivatives of 5,6,7,8‐Tetrahydro‐1‐naphthylamine and 5,6,7,8‐Tetrahydro‐2‐naphthylamine** 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 acid (**2**), 4‐amino‐5,6