Potassium Hydroxide → HCID 15366238, compound

HRID 21585Notes

Reaction equation

HRID 21585 reaction equation
[OH-].[K+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[N:6]([CH3:21])[C:5]=1[C:22]([O:24]CC)=[O:23]>CO>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[N:6]([CH3:21])[C:5]=1[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15366237Ethyl 3-bromo-1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 15366238HCID 15366238, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of potassium hydroxide (17.0 g, 303 mmol) in 3.0 L of 50% aqueous methanol is treated with ethyl 3-bromo-1-methyl-5-(phenylmethoxy)-1 H-indole-2-carboxylate (55.4 g, 143 mmol). The mixture is stirred at reflux for 5 hours, than decanted while warm from any insoluble material into 600 mL of hot water. The warm solution is quickly acidified with 100 mL of 4.0N HCl. An additional 1.0 L of cold water is added, and the mixture is stirred for 1 hour. The precipitated solid is filtered, stirred in 1.0 L of 25% methanol-water, and refiltered, to give 49.6 g (96%) of product, suitable for further synthesis. A sample recrystallized from aqueous acetonitrile has mp 210° C.-dec.

Workup

  1. temperatureat reflux for 5 hours
  2. customthan decanted
  3. temperaturewhile warm from any insoluble material into 600 mL of hot water
  4. additionAn additional 1.0 L of cold water is added
  5. stirringthe mixture is stirred for 1 hour
  6. filtrationThe precipitated solid is filtered
  7. stirringstirred in 1.0 L of 25% methanol-water

Sources & evidence

ORD record
ord-b1ffc0d85f5646f68856fecdb33030b6
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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