Ethanol → HCID 21838717, compound

HRID 1740504Notes

Reaction equation

HRID 1740504 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[N:9]([CH3:24])[C:8]=1[C:25]([O:27]CC)=[O:26])=[O:5])[CH3:2].C(O)C.[OH-].[K+]>O1CCCC1>[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[N:9]([CH3:24])[C:8]=1[C:25]([OH:27])=[O:26])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21838705HCID 21838705, compound

Product 1

HCID 21838717HCID 21838717, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 28.1 g (0.0708 mol) of ethyl 3-[(ethoxycarbonyl)amino]-1-methyl-6-(phenylmethoxy)-1H-indole-2-carboxylate in 170 ml of 96° ethanol is brought to reflux. 64 ml of a 10% ethanolic potassium hydroxide solution and 50 ml of tetrahydrofuran are added to this mixture. The suspension is left at reflux for 150 min, is then concentrated under reduced pressure, diluted with a mixture of water and ice and acidified with 6N hydrochloric acid. The product is then extracted with a mixture of dichloromethane and tetrahydrofuran, the organic phase is washed with water and dried over sodium sulphate and the solvent is evaporated under reduced pressure. The residue is triturated in diisopropyl ether and 24.8 g of product are recovered.

Workup

  1. temperatureto reflux
  2. waitThe suspension is left
  3. temperatureat reflux for 150 min
  4. concentrationis then concentrated under reduced pressure
  5. additiondiluted with a mixture of water and ice
  6. extractionThe product is then extracted with a mixture of dichloromethane and tetrahydrofuran
  7. washthe organic phase is washed with water
  8. dry with materialdried over sodium sulphate
  9. customthe solvent is evaporated under reduced pressure
  10. customThe residue is triturated in diisopropyl ether
  11. custom24.8 g of product are recovered

Sources & evidence

ORD record
ord-5c2e9043b4a24620b5ce99caf73e883c
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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