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Methanol → 1-(4-Methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylic acid

HRID 1942538
Notes
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Reaction equation

HRID 1942538 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18]C)=[O:17])[CH:14]=2)[C:9]([CH3:21])([CH3:20])[C:8]1=[O:22].[OH-].[Na+].CO>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=2)[C:9]([CH3:20])([CH3:21])[C:8]1=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67330620Methyl 1-(4-methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylate

Product 1

HCID 673310081-(4-Methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To methyl 1-(4-methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylate (480 mg) were added 2N aqueous NaOH solution (5 ml), MeOH (5 ml), and THF (5 ml), and the mixture was stirred at 65° C. for one hour. After the reaction was complete, the solvent was concentrated, and to the resultant was added dropwise 2N aqueous hydrochloric acid solution. The precipitated crystals were extracted with ethyl acetate, and this ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue (400 mg) was used in the subsequent reaction without further treatment.

Workup

  1. concentrationthe solvent was concentrated
  2. additionto the resultant was added dropwise 2N aqueous hydrochloric acid solution
  3. extractionThe precipitated crystals were extracted with ethyl acetate
  4. washthis ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue (400 mg) was used in the subsequent reaction without further treatment

Sources & evidence

ORD record
ord-910e1a4e7a7f408c97c4b501b9c5980e
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08389511B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes