Hydrochloric Acid → 3-(hydroxymethylidene)-1H-indol-2-one

HRID 492159Notes

Reaction equation

HRID 492159 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11](OCC)=[O:12].CC[O-].[Na+].Cl>CCO.O>[OH:12][CH:11]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 321710OxindoleHCID 2723922Sodium ethoxide

Product 1

HCID 1784187413-(hydroxymethylidene)-1H-indol-2-oneYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a slurry of oxindole (1.33 g, 10.0 mmol) and ethyl formate (2.42 mL, 30.0 mmol) was added 4.85 mL of 21 wt. % NaOEt in EtOH. The thick solution was stirred for 30 min at room temperature and then heated at reflux for 30 min. The solution was acidified to pH=3 with 10% aqueous HCl and 5 mL H2O was added. The solid which formed was filtered and rinsed with H2O to give the title compound (1.34 g, 83%) as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 min
  3. additionwas added
  4. customThe solid which formed
  5. filtrationwas filtered
  6. washrinsed with H2O

Sources & evidence

ORD record
ord-008c2e5f5a904db295a6d085ff0cad25
Source dataset
uspto-grants-2009_05
Patent number
US07531665B2

Reaction notes

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