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

HRID 420148Notes

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

Participants

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

temperatureThe mixture was cooled
filtrationThe precipitate was filtered
customcollected
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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