Acetic Acid → 5-(3,5-Dimethylisoxazol-4-yl)-7-methoxyindoline-2,3-dione

HRID 1052984Notes

Reaction equation

HRID 1052984 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([O:16][CH3:17])[CH:15]=2)[NH:12][C:11](=[O:18])[C:10]23OCC[O:19]2)=[C:5]([CH3:23])[O:4][N:3]=1.C(O)(=O)C.Cl>CCOC(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([O:16][CH3:17])[CH:15]=2)[NH:12][C:11](=[O:18])[C:10]3=[O:19])=[C:5]([CH3:23])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1176681035'-(3,5-Dimethylisoxazol-4-yl)-7'-methoxyspiro[[1,3]dioxolane-2,3'-indolin]-2'-one

Product 1

HCID 1176681345-(3,5-Dimethylisoxazol-4-yl)-7-methoxyindoline-2,3-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 5′-(3,5-dimethylisoxazol-4-yl)-7′-methoxyspiro[[1,3]dioxolane-2,3′-indolin]-2′-one (57 mg, 0.18 mmol), acetic acid (1 mL), and hydrogen chloride solution (4 mL) was heated to 90° C. After 1.5 h, the mixture was cooled, EtOAc (20 mL) was added, washed with brine (15 mL×3), dried over Na2SO4, concentrated in vacuo to give the expected compound 5-(3,5-dimethylisoxazol-4-yl)-7-methoxyindoline-2,3-dione as a dark red solid (50 mg, crude, 102%). This material was used in the next step without further purification. MS (ESI) m/e [M+1]+ 273.

Workup

  1. temperaturethe mixture was cooled
  2. washwashed with brine (15 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8495814ad5a24db6b702f3f6db0c631f
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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