Potassium Hydroxide → HCID 18367851, compound

HRID 379819Notes

Reaction equation

HRID 379819 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7](C(OCC)=O)[C:6]=1[C:20]([O:22]C)=[O:21])(=[O:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:20]([OH:22])=[O:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54164021HCID 54164021, compound

Product 1

HCID 18367851HCID 18367851, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-acetylamino-6-chloro-1-(ethoxycarbonyl)indole-2-carboxylate (step 2; 1.48 g, 4.37 mmol) dissolved in ethanol (20 ml) and 1N aqueous KOH (10 ml) were heated together at reflux for 1 h. The mixture was cooled and concentrated, and the residue diluted with 1N aqueous HCl (20 ml) and extracted with ethyl acetate (30 ml×2). The organic extract was dried (MgSO4) and evaporated to afford 0.95 g (86%) of the title compound as a white solid.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. additionthe residue diluted with 1N aqueous HCl (20 ml)
  5. extractionextracted with ethyl acetate (30 ml×2)
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-c33973afc0484002b8611597348da3ed
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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