Potassium Hydroxide → 1-(2-Diethylaminoethyl)-3-hydroxy-3(2-chlorophenyl)-4-bromo-6-carbamoyloxindole

HRID 1369098Notes

Reaction equation

HRID 1369098 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([Br:17])[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([OH:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:7]1=[O:26])[CH3:2].[OH-:29].[K+]>CC(O)(C)C>[CH2:27]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([Br:17])[CH:11]=[C:12]([C:15](=[O:29])[NH2:16])[CH:13]=2)[C:8]([OH:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:7]1=[O:26])[CH3:28]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 185185971-(2-Diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-cyanooxindole

Product 1

HCID 185185551-(2-Diethylaminoethyl)-3-hydroxy-3(2-chlorophenyl)-4-bromo-6-carbamoyloxindoleYield 69%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-cyanooxindole (462.6 mg, 1.06 mmol) dissolved in anhydrous t-BuOH (30 mL) at 50° C. was added powdered KOH (1.2 g, 20 eq). The resulting solution was stirred for 1 hour and then cooled to room temperature. Ice was added and the mixture extracted with EtOAc (3×20 mL). The extracts were combined and dried (anhydrous MgSO4). After filtration, the solvent was removed in vacuo to give a light brown solid. Purification was carried out by column chromatography (silica gel, eluting EtOAc:EtOH:Et3N, 80:20:2) to yield the title compound as a white solid (346.5 mg, 69%).

Workup

  1. additionIce was added
  2. extractionthe mixture extracted with EtOAc (3×20 mL)
  3. dry with materialdried (anhydrous MgSO4)
  4. filtrationAfter filtration
  5. customthe solvent was removed in vacuo
  6. customto give a light brown solid
  7. customPurification
  8. washwas carried out by column chromatography (silica gel, eluting EtOAc:EtOH:Et3N, 80:20:2)

Sources & evidence

ORD record
ord-50890c9bc5db4643b7f954a4902e8648
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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