Application of 14389-06-1, The chemical industry reduces the impact on the environment during synthesis 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.
To a suspension of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 13.02 g, 42 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 72(17), pp 2427-2430) (7.82 g, 40 mmol) in dry acetonitrile (50 mL) was added 3-picoline (11.9 g, 127 mmol). The mixture was cooled to 0 C, and then methanesulfonyl chloride (6.87 g, 60 mmol) was added dropwise at 0-10 0C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 20 hours. The precipitated solids were filtered, washed with acetonitrile (3 x 5 mL), and dried under nitrogen to afford the title product, a compound of the present invention, as a yellow powder, 14.90 g (77.6% yield), m.p. 173-177 0C (decomp.).1H NMR (CDCl3) delta 2.16 (s, 3H), 7.14 (s, IH), 7.38 (dd, J = 8.1, 4.8 Hz, IH), 7.53 (d, /= 2.1 Hz, IH), 7.60 (d, /= 2.1 Hz, IH), 7.89 (dd, /= 8.1, 1.5 Hz, IH), 8.39 (dd, / = 4.8, 1.5 Hz, IH). The NMR spectrum also showed that some 3-picoline salts were present in the crude product.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Chloro-7-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/24833; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem