Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.
The above material was dissolved in methanol (50 mL) and formic acid (5 miL) and hydrogenated over Pd/C (0.40 g) at elevated hydrogen pressure (50 psi) for 16 h. The reaction mixture was filtered through a plug of celite (10 g), the celite was washed with methanol (2X20 ML), the combined filtrates were evaporated to dryness, dissolved in H20 (20 mL), and re-evaporated. The resulting residue was dissolved in N, N-DIMETHYLFORMAMIDE (5 mL), and added in one portion to the previously prepared suspension of 2-oxoindoline-5-carboxylic acid (0.53 g, 3 MMOL), O-(BENZOTRIAZOL-L-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (1.1 g, 3.6 mmol), 1-HYDROXYBENZOTRIAZOLE (0.486 g, 3.6 mmol) and N,N-diisopropylethylamine (1.7 g, 12 mmol) in acetonitrile (10 ML) and N,N-dimethylformamide (10 mL). The mixture was stirred overnight, the solvents were removed in vacuo, and the residue was purified on a silica gel column using chloroform/methanol, (10: 1), then CHLOROFORM/METHANOL/AQUEOUS ammonia, (100: 10: 1), as the eluent. The semi-solid crude material was again subjected to silica gel chromatography using chloroform/methanol/aqueous ammonia, (150: 10: 1), as the eluent to afford 0.20 g (19% yield) the title compound as yellow foam: MS (ES) M/Z 367 (M++1).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem