Potassium Hydroxide → HCID 18344915, compound

HRID 2301328Notes

Reaction equation

HRID 2301328 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:21])=[C:12]([CH2:15][C:16]([O:18]CC)=[O:17])[CH:13]=2)[NH:8][C:7]=1[CH3:22])=[O:5])[CH3:2].[OH-].[K+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:21])=[C:12]([CH2:15][C:16]([OH:18])=[O:17])[CH:13]=2)[NH:8][C:7]=1[CH3:22])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18344919HCID 18344919, compound

Product 1

HCID 18344915HCID 18344915, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 6-bromo-5-ethoxycarbonylmethyl-2-methyl-1H-indole-3-carboxylic acid ethyl ester (3 g, 8.1 mmol) in ethanol (30 mL) is added 4.6N KOH (3 mL; 9.8 mmol), and the reaction mixture is stirred at 45° C. for 4 hours and then at room temperature overnight. The solution is concentrated in vacuo and then ethyl acetate (150 mL) and water (150 mL) are added. The organic layer is extracted with water (50 mL), the combined water layers are then acidified with HCl (20%) to pH<2. The aqueous layers are then extracted with ethyl acetate (2×100 mL), dried (Na2SO4), filtered, and concentrated to give the desired product (1.85 g, 66%). MS: 340, 342 (M+1)+.

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationThe solution is concentrated in vacuo
  4. additionethyl acetate (150 mL) and water (150 mL) are added
  5. extractionThe organic layer is extracted with water (50 mL)
  6. extractionThe aqueous layers are then extracted with ethyl acetate (2×100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-02cd5578f43c476d83dd93e775bda0b6
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

Loading…