Potassium Hydroxide → 3-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]furan-2,5-dione

HRID 1017563Notes

Reaction equation

HRID 1017563 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:33])N(C)[C:14](=[O:31])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:17]=2)=[CH:3]1.[OH-:34].[K+]>CCO.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:34])[O:33][C:14](=[O:31])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH:17]=2)=[CH:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 184035183-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1-methylpyrrole-2,5-dione

Product 1

HCID 120181343-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]furan-2,5-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1-methylpyrrole-2,5-dione (0.22 g, 0.5 mmol) was dissolved in EtOH (10 mL) and a solution of KOH (1.5 g) in H2O (2.5 mL) was added. After the reaction mixture was refluxed for 3 h, it was cooled to room temperature, followed by evaporation of EtOH. The residue was acidified with aq. HCl to pH=4.5. The product was extracted with EtOAc and the EtOAc layer was dried over sodium sulfate and concentrated to give 3-(1-methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]furan-2,5-dione which was in the next step without further purification.

Workup

  1. temperatureAfter the reaction mixture was refluxed for 3 h
  2. customfollowed by evaporation of EtOH
  3. extractionThe product was extracted with EtOAc
  4. dry with materialthe EtOAc layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d861b6b2d8044ef7b0301e74732083aa
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

Loading…