Potassium Hydroxide → HCID 10848352, compound

HRID 21582Notes

Reaction equation

HRID 21582 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13]([O:15]C)=[O:14])=[C:6]2[S:17][CH3:18].[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13]([OH:15])=[O:14])=[C:6]2[S:17][CH3:18]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10730410Methyl 5-methoxy-1-methyl-3-(methylthio)-1H-indole-2-carboxylate

Product 1

HCID 10848352HCID 10848352, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A suspension of methyl 5-methoxy-1-methyl-3-(methylthio)-1H-indole-2-carboxylate (3.2 g, 12 mmol) in 65 mL of methanol is treated with a solution of potassium hydroxide (2.5 g, 45 mmol) in 25 mL of water. The mixture is stirred at reflux for 2 hours, then cooled and added to 400 g of ice and water. After washing with dichloromethane, the aqueous layer is stirred with celite filter-aid and filtered. The filtrate is acidified with 4.0N HCl and the precipitated solid is filtered and washed with 10% methanol-water to yield 2.6 g (87%) of product. A sample recrystallized from hexane-ethyl acetate has mp 165° C.-dec.

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled
  3. washAfter washing with dichloromethane
  4. stirringthe aqueous layer is stirred
  5. filtrationwith celite filter-aid
  6. filtrationfiltered
  7. filtrationthe precipitated solid is filtered
  8. washwashed with 10% methanol-water

Sources & evidence

ORD record
ord-890c1f982758412a9590f591a64b7d78
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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