p-Toluenesulfonic acid monohydrate → HCID 67154076, compound

HRID 1400131Notes

Reaction equation

HRID 1400131 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]3)[CH:8]=2)[NH:3]1.O.[C:19]1(C)C=CC(S(O)(=O)=O)=C[CH:20]=1>C(O)C>[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([C:15]([O:17][CH2:19][CH3:20])=[O:16])[CH2:14][CH2:13]3)[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67154084HCID 67154084, compound

Product 1

HCID 67154076HCID 67154076, compoundYield 983.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6.5 g of (2,3-dioxo-2,3-dihydro-1H-indol-5-yl)cyclopropanecarboxylic acid are dissolved in 100 ml of ethanol, and 500 mg of toluene-4-sulfonic acid monohydrate are added. The mixture is heated at 80° C. for 1 h and subsequently evaporated 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 6.7 g (92%) of ethyl 1-(2,3-dioxoindolin-5-yl)cyclopropanecarboxylate; LC-MS retention time: 1.30 min.

Workup

  1. customsubsequently evaporated 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-bac61239ef4346b0832d8b6eae2477e3
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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