ethyl-3-chloro-1-cyclopropyl-4-(methoxy)-1H-indole-6-carboxylate → 3-chloro-1-cyclopropyl-4-(methyloxy)-1H-indole-6-carboxylic acid

HRID 420147Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([Cl:18])=[CH:11][N:12]2[CH:15]2[CH2:17][CH2:16]2)=[C:8]([O:19][CH3:20])[CH:7]=1)=[O:5])C>CO.C1COCC1>[Cl:18][C:10]1[C:9]2[C:13](=[CH:14][C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[O:19][CH3:20])[N:12]([CH:15]2[CH2:17][CH2:16]2)[CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 1.03 g of ethyl-3-chloro-1-cyclopropyl-4-(methyloxy)-1H-indole-6-carboxylate in 15 ml of MeOH and 10 ml of THF was added 2 ml of 5N NaOHaq and the mixture was stirred at 60° C. for 9 hrs. After evaporation of MeOH and THF, the mixture was diluted with water and 2 ml of 5N HClaq was added thereto. The precipitate was collected by filtration and dried in vacuo to give 798 mg of 3-chloro-1-cyclopropyl-4-(methyloxy)-1H-indole-6-carboxylic acid as a colorless solid.

Workup

customAfter evaporation of MeOH and THF
additionthe mixture was diluted with water and 2 ml of 5N HClaq
additionwas added
filtrationThe precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-9c5e09cdffb047ce96567cf04e73f502
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093389B2

Reaction notes

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