Hydrochloric Acid → 5-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dione

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Reaction Steps

A solution of compound 5′-(3,5-dimethylisoxazol-4-yl)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one (150 g, 0.52 mol), acetic acid (10 mL), and concentrated HCl solution (300 mL) was heated to 90° C. After 1 h, the mixture was poured into ice-water, and the expected compound 5-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dione was collected by filtration and washed with water, EtOH, and EtOAc, and afforded target compound (115 g, 92%). 1H NMR (DMSO-d6) δH 11.14 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.51 (s, 1H), 7.00 (d, J=8.0 Hz, 1H), 2.37 (s, 3H), 2.20 (s, 3H). MS (ESI) m/e [M+1]+ 243.

Provenance & Evidence