Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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. 3484-35-3
4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 65 mg (42%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.30 (s, br, 1 H, NH-1′), 12.05 (s, br, 1 H, COOH), 10.67 (s, br, 1 H, NH-1), 7.57 (s, 2 H, H-vinyl, H-4), 7.12 (d, J=2.65 Hz, 1 H, H-2′), 6.91 (d, J=7.82 Hz, 1 H, H-6), 6.74 (d, J=7.82 Hz, 1 H, H-7), 2.65 (t, J=6.94 Hz, 2 H, CH2CH2COOH), 2.46 (t, J=6.94 Hz, 2 H, CH2CH2COOH), 2.30 (s, 3 H, CH3), 2.25 (s, 3 H, CH3); MS m/z (relative intensity, %) 311 ([M+1]+, 100).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3484-35-3, its application will become more common.
Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem