Hydrochloric Acid → (2E)-3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-7-yl)acrylic acid

HRID 1097438Notes

Reaction equation

HRID 1097438 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2/[CH:11]=[CH:12]/[C:13]([O:15]CC)=[O:14])[C:4]([CH3:19])([CH3:18])[C:3]1=[O:20].[OH-].[Na+].Cl>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[C:4]([CH3:18])([CH3:19])[C:3]1=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66812761Ethyl (2E)-3-(1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-7-yl)acrylate

Product 1

HCID 59322842(2E)-3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-7-yl)acrylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2E)-3-(1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-7-yl)acrylate (25 mg, 0.091 mmol) in MeOH (1 mL) was added 1 N aqueous NaOH (0.1 mL) and the resulting mixture was stirred at ambient temperature for 18 h. To the reaction mixture was added 1 N aqueous HCl (0.1 mL) and the resulting mixture was concentrated to dryness under reduced pressure to give the title compound. MS: m/z=246 (M+1).

Workup

  1. concentrationthe resulting mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-664873fb9f5940c4a2761d4143789d53
Source dataset
uspto-grants-2012_03
Patent number
US08143266B2

Reaction notes

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