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Hydrochloric Acid → 3,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid

HRID 704628
Notes
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Reaction equation

HRID 704628 reaction equation
[OH-:1].[Na+].[Cl-].[CH3:4][C:5]1([CH3:24])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14](=[O:22])C[N+]3C=CC=CC=3)[CH:12]=2)[NH:7][C:6]1=[O:23].Cl>O>[CH3:24][C:5]1([CH3:4])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:22])=[O:1])[CH:12]=2)[NH:7][C:6]1=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 200728801-[2-(2,3-Dihydro-3,3-dimethyl-2-oxoindol-5-yl)-2-oxoethyl]pyridinium chloride

Product 1

HCID 150778053,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (14 g) in water (480 ml) was added 1-[2-(2,3-dihydro-3,3-dimethyl-2-oxoindol-5-yl)-2-oxoethyl]pyridinium chloride (44.3 g) and the mixture was stirred for 1.5 hours at 80° to 85° C. After cooling, the reaction mixture was acidified with conc. hydrochloric acid. The residual crystal was collected by filtration, washed with water and dried to give 2,3-dihydro-3,3-dimethyl-2-oxoindole-5-carboxylic acid (21 g).

Workup

  1. temperatureAfter cooling
  2. filtrationThe residual crystal was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0e2bb4ff98e8454c913961c77c3ad3d0
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04988698

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes