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

HRID 1052954Notes

Reaction equation

HRID 1052954 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]23OCC[O:17]2)=[C:5]([CH3:21])[O:4][N:3]=1.Cl>C(O)(=O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3=[O:17])=[C:5]([CH3:21])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1176683845'-(3,5-Dimethylisoxazol-4-yl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one

Product 1

HCID 1175999855-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. filtrationthe expected compound 5-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dione was collected by filtration
  2. washwashed with water, EtOH, and EtOAc

Sources & evidence

ORD record
ord-bd09f5c405ba404d8163d9443b84f359
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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