Water → HCID 15462807, compound

HRID 1421257Notes

Reaction equation

HRID 1421257 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[C:10]=2[C:28]([O:30]CC)=[O:29])=[CH:5][CH:4]=1.[OH-].[Na+].O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[C:10]=2[C:28]([OH:30])=[O:29])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15462806HCID 15462806, compound

Product 1

HCID 15462807HCID 15462807, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(4-methoxyphenyl)-1-(3,4-methylenedioxybenzyl)-pyrrolo[2,3-b]pyridine-2-carboxylate in EtOH with aqueous 1 N NaOH is stirred under an argon atmosphere first at room temperature then at reflux temperature. The reaction mixture is cooled to room temperature then poured into H2O and the solvent volume reduced in vacuo. The aqueous solution is extracted with Et2O and the Et2O extract discarded. The aqueous layer is acidified with 6 N HCl and the product extracted into EtOAc. The organic extract is washed with H2O then saturated aqueous NaCl, dried (Na2SO4) and the solvent removed in vacuo to afford the title compound.

Workup

  1. temperatureat reflux temperature
  2. extractionThe aqueous solution is extracted with Et2O
  3. extractionthe Et2O extract
  4. extractionthe product extracted into EtOAc
  5. extractionThe organic extract
  6. washis washed with H2O
  7. dry with materialsaturated aqueous NaCl, dried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9e450ed2c7084929aead9e904695ad5f
Source dataset
uspto-grants-2000_06
Patent number
US06075037

Reaction notes

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