p-Toluenesulfonic acid → Methyl 1-acetyl-3-methoxyindole-6-carboxylate

HRID 23945Notes

Reaction equation

HRID 23945 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6](=[O:17])[CH2:5]1)(=[O:3])[CH3:2].[CH:18](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([O:17][CH3:18])=[CH:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 22570063HCID 22570063, compound

Product 1

HCID 22569986Methyl 1-acetyl-3-methoxyindole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-acetyl-2,3-dihydroindol-3-one-6-carboxylate (233 mg, 1 mmol), trimethyl orthoformate (10 ml) and p-toluene sulphonic acid (20 mg) were heated under reflux for 3 h. in methanol (10 ml). The reaction mixture was concentrated under reduced pressure, poured into water and extracted with chloroform. After drying and evaporation, the product was purified by prep hplc;

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionpoured into water
  3. extractionextracted with chloroform
  4. customAfter drying
  5. customevaporation
  6. customthe product was purified by prep hplc

Sources & evidence

ORD record
ord-1f0d3c3ac8c7474ba821015aa76506fe
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Reaction notes

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