Ethanol → HCID 21891630, compound

HRID 720337Notes

Reaction equation

HRID 720337 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[C:14]=3OC)[CH:9]=[C:8]2[C:22]([O:24]C)=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH2:28]([OH:30])C>>[C:1]1([N:7]2[C:15]3[C:10](=[C:11]([O:30][CH3:28])[C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=[C:8]2[C:22]([OH:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21891640HCID 21891640, compound

Product 1

HCID 21891630HCID 21891630, compound

Procedure

Methyl 1-phenyl-5,6,7-trimethoxyindole-2-carboxylate (280 mg) was dissolved in ethanol (5 mL), a 10% aqueous solution (2 mL) of potassium hydroxide was added to the solution, and the mixture was stirred for 30 minutes under reflux. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water and washed with ether. The water layer was then neutralized with hydrochloric acid and extracted with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washwashed with ether
  6. extractionextracted with ethyl acetate
  7. washThe resultant organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bedccbddc9947278b8cbd39b613fe06
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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