Category: 1885-29-6

Electric Literature of 1885-29-6, A common heterocyclic compound, 1885-29-6, name is 2-Aminobenzonitrile, molecular formula is C7H6N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 2-aminobenzonitrile (5 g, 42.3 mmol) and NBS (16.57g, 93.1 mmol, 2.2 equiv) was refluxed in MeCN (80 mL) for 3 h. After cooling, the precipitate formed was filtered, washed with H2O (3 × 60 mL), and dried in a vacuum drying oven (desiccator cabinet). Recrystallization from propan-2-ol gave 1 as a brown solid; yield: 8.9 g (77%); mp 158 C (Lit.14 mp 156 C). 1H NMR (200 MHz, CDCl3): delta = 4.91 (s, 2 H, NH2), 7.47 (d, J = 2.1Hz, 1 H, H-4), 7.71 (d, J = 2.1 Hz, 1 H, H-6). 13C NMR (50 MHz, CDCl3): delta = 97.9, 108.2, 109.7, 115.6, 133.6,139.4, 146.2.

The synthetic route of 1885-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kabri, Youssef; Crozet, Maxime D.; Redon, Sebastien; Vanelle, Patrice; Synthesis; vol. 46; 12; (2014); p. 1613 – 1620;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1885-29-6, name is 2-Aminobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1885-29-6, Quality Control of 2-Aminobenzonitrile

Bromine (110 mmol, 5.6 mL) was added dropwise to an acetic acid solution (150 mL) of 2-aminobenzonitrile (50 mmol, 5.9 g) in an argon atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice water (200 mL), and the resulting solid was collected by filtration and washed with water.The residue was recrystallized from ethyl acetate to obtain 2-amino-3,5-dibromobenzonitrile (6.9 g, yield 50%).The obtained 2-amino-3,5-dibromobenzonitrile (10.0 mmol, 2.75 g), tetrabutylammonium fluoride trihydrate (5.0 mmol, 1.58 g), trimethylsilyl azide (TMSN3) (15 0.0 mmol, 2.0 mL) was stirred at 85 C. for 2 hours under an argon atmosphere. Ethyl acetate was added to the reaction solution, and the mixture was extracted 3 times with 1M hydrochloric acid (5 mL), and then the organic layer was dried over magnesium sulfate and dried under reduced pressure.Ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate: ethanol = 10: 1), and 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.40 g, yield 44%) was white. Obtained as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Aminobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts