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Hydrochloric Acid → 1-cyclopropyl-4-methoxy-3-methyl-1H-indole-6-carboxylic acid

HRID 420148
Notes
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Reaction equation

HRID 420148 reaction equation
[OH-].[Na+].[CH:3]1([N:6]2[C:14]3[C:9](=[C:10]([O:20][CH3:21])[CH:11]=[C:12]([C:15]([O:17]CC)=[O:16])[CH:13]=3)[C:8]([CH3:22])=[CH:7]2)[CH2:5][CH2:4]1.Cl>CO>[CH:3]1([N:6]2[C:14]3[C:9](=[C:10]([O:20][CH3:21])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=3)[C:8]([CH3:22])=[CH:7]2)[CH2:4][CH2:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66649525Ethyl 1-cyclopropyl-3-methyl-4-methoxy-1H-indole-6-carboxylate

Product 1

HCID 569716581-cyclopropyl-4-methoxy-3-methyl-1H-indole-6-carboxylic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4.66 mL of 5 N NaOH aqueous was added to a solution of 3.19 g of ethyl 1-cyclopropyl-3-methyl-4-methoxy-1H-indole-6-carboxylate in 32 mL of MeOH and the mixture was stirred at 60° C. overnight. The mixture was cooled and 46.6 mL of 1N HCl was added thereto. The precipitate was filtered, collected and dried in vacuo to afford 2.70 g of 1-Cyclopropyl-3-methyl-4-methoxy-1H-indole-6-carboxylic acid as a colorless solid.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitate was filtered
  3. customcollected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c14221621cd14b9f9dbaa03c7644f708
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093389B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes