HCID 291853, compound → HCID 68227176, compound

HRID 1400120Notes

Reaction equation

HRID 1400120 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:8]=2)[NH:3]1.O.[C:17]1(C)C=CC(S(O)(=O)=O)=C[CH:18]=1>C(O)C>[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][C:13]([O:15][CH2:17][CH3:18])=[O:14])[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 291853HCID 291853, compoundHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 68227176HCID 68227176, compoundYield 1,114.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4 g of (2,3-dioxo-2,3-dihydro-1H-indol-5-yl)acetic acid are dissolved in 100 ml of ethanol, and 300 mg of toluene-4-sulfonic acid monohydrate are added. The mixture is heated at 80° C. for 1 h, and the solvent is subsequently removed in vacuo. The residue is taken up in 100 ml of water and 100 ml of ethyl acetate and stirred at 60° C. for a further 12 h. The mixture is neutralised using sodium hydrogencarbonate, and the organic phase is separated off. The aqueous phase is washed a further twice with 100 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated to dryness in vacuo, giving 4.1 g of ethyl 2-(2,3-dioxoindolin-5-yl)acetate;

Workup

  1. customthe solvent is subsequently removed in vacuo
  2. customthe organic phase is separated off
  3. washThe aqueous phase is washed a further twice with 100 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-f9f7cb8dea4b44648e1aa4d7f8890c9e
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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