HCID 86681655, compound → HCID 83755600, compound

HRID 571240Notes

Reaction equation

HRID 571240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]C)=[O:14])[C:7](=[O:17])[CH2:6]2>O1CCOCC1.Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7](=[O:17])[CH2:6]2

Participants

4

Reactant 1

HCID 86681655HCID 86681655, compound

Product 1

HCID 83755600HCID 83755600, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 2-(5-methoxy-2-oxoindolin-1-yl)acetate (350 mg, 1.488 mmol) in dioxane (10 ml), 12N HCl (10 ml) was added, and the mixture was stirred at room temperature for 24 hours. Then the solvent was evaporated and the resulting crude was dissolved in MeOH (5 ml); by addition of iPrO2 (50 ml) the title compound precipitated, was filtered and used in the next step without further purification (200 mg, 0.904 mmol, 61% yield). MS/ESI+ 222.2 [MH]+.

Workup

  1. customThen the solvent was evaporated
  2. dissolutionthe resulting crude was dissolved in MeOH (5 ml)
  3. additionby addition of iPrO2 (50 ml) the title compound
  4. customprecipitated
  5. filtrationwas filtered
  6. customused in the next step without further purification (200 mg, 0.904 mmol, 61% yield)

Sources & evidence

ORD record
ord-4350ac8c3f6b4edc9e2e1314168747ae
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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