Sodium Hydroxide → HCID 13234032, compound

HRID 1632508Notes

Reaction equation

HRID 1632508 reaction equation
C(OC([C:6]1([OH:22])[C:14]2[C:9](=[CH:10][C:11]([CH3:20])=[C:12]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH:13]=2)[NH:8]C1=O)=O)C.[OH-:23].[Na+]>CO>[C:15]([C:12]1[CH:13]=[C:14]([C:6]([OH:22])=[O:23])[C:9]([NH2:8])=[CH:10][C:11]=1[CH3:20])(=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13234031HCID 13234031, compound

Product 1

HCID 13234032HCID 13234032, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.0 g of 5-butyryl-3-hydroxy-6-methyloxindole-3-carboxylic acid ethyl ester are suspended in 200 ml of methanol and 85 ml of 2N sodium hydroxide solution are added. The mixture is stirred at room temperature for 90 minutes, the methanol is removed under reduced pressure, the mixture is acidified to pH 3-4 with 2N hydrochloric acid, filtered with suction, then the residue is washed with water, dissolved in ethyl acetate, dried over magnesium sulphate, concentrated to dryness by evaporation under reduced pressure, digested with a little methylene chloride and filtered with suction. 5-Butyryl-4-methylanthranilic acid having a melting point of 184°-186° is obtained.

Workup

  1. customthe methanol is removed under reduced pressure
  2. filtrationfiltered with suction
  3. washthe residue is washed with water
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness by evaporation under reduced pressure
  7. filtrationfiltered with suction

Sources & evidence

ORD record
ord-ac5b54767cbf4ef584b492e0e6fcd522
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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