Potassium Hydroxide → HCID 22013003, compound

HRID 618544Notes

Reaction equation

HRID 618544 reaction equation
[OH-].[K+].C([O:5][C:6]([CH2:8][C:9]1([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18])=[O:7])C>O.C(O)C>[OH:7][C:6]([CH2:8][C:9]1([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22013034HCID 22013034, compound

Product 1

HCID 22013003HCID 22013003, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 300 mg of potassium hydroxide (85%) in 2 ml of water was added to a solution of 0.35 g of (RS)-3-(ethoxycarbonylmethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one in 10 ml of ethanol at room temperature, and the mixture was stirred for 4 hours, followed by concentration. The concentrate was diluted with water, and washed with chloroform. The aqueous layer was adjusted to pH 3 by addition of 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The resulting crude product was recrystallized from isopropyl alcohol to give 0.088 g (27%) of the title compound.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with water
  3. washwashed with chloroform
  4. additionThe aqueous layer was adjusted to pH 3 by addition of 2N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting crude product was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5bf27a53bac74d4ea0221ea29ffcf646
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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