Sodium Hydroxide → HCID 70145434, compound

HRID 442855Notes

Reaction equation

HRID 442855 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][O:39][CH3:40])=[CH:33][CH:32]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:13]=2[C:26]([O:28]CC)=[O:27])=[CH:7][CH:6]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH2:38][O:39][CH3:40])=[CH:35][CH:36]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[C:13]=2[C:26]([OH:28])=[O:27])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70144374HCID 70144374, compound

Product 1

HCID 70145434HCID 70145434, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude ethyl 3-{bis[4-(methoxymethoxy)phenyl]methyl}-1-(2-dimethylaminoethyl)indole-2-carboxylate (16.4 g, approximately 27.0 mmol) obtained in Example 47 was dissolved in 100 ml of ethanol, and a 2N aqueous sodium hydroxide solution (40 ml) was added thereto, followed by heating under reflux for 3 hours. The solvent was distilled off under reduced pressure, water was added to dissolve the residue, and the pH of the solution was adjusted to 5 by adding 2N hydrochloric acid, followed by extraction with chloroform. The resulting organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 14.4 g of a crude product. The obtained crude product was crystallized from ethyl acetate to give 8.9 g (yield: 64%) of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. distillationThe solvent was distilled off under reduced pressure, water
  4. additionwas added
  5. dissolutionto dissolve the residue
  6. additionby adding 2N hydrochloric acid
  7. extractionfollowed by extraction with chloroform
  8. washThe resulting organic layer was washed with water
  9. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customto give 14.4 g of a crude product
  12. customThe obtained crude product
  13. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-105180ac318347dd83c082af03f8273f
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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