Hydrochloric Acid → 5-(Trifluoromethyl)-1H-indole-3-carboxylic acid

HRID 2264620Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]([O:14]C)=[O:13].Cl.O>CO.C1COCC1.[OH-].[Na+]>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.01 g of methyl 5-(trifluoromethyl)-1H-indole-3-carboxylate in 12 mL of MeOH and 12 mL of THF, 6 mL of 1 M aqueous sodium hydroxide solution was added, and the resulting mixture was stirred at 80° C. overnight. To the solution, 3 mL of 1 M aqueous sodium hydroxide solution was further added, and the resulting mixture was stirred at 80° C. for 6 hours. To the solution, 9 mL of 1 M hydrochloric acid and 60 mL of water were added, the precipitated solid was collected by filtration, and the solid obtained was purified by silica gel column chromatography (chloroform-methanol=100:1 →150:1→20:1) and then washed with hexane to obtain 0.71 g of 5-(trifluoromethyl)-1H-indole-3-carboxylic acid as a cream-colored solid. FAB−: 228

Workup

stirringthe resulting mixture was stirred at 80° C. for 6 hours
filtrationthe precipitated solid was collected by filtration
customthe solid obtained
customwas purified by silica gel column chromatography (chloroform-methanol=100:1 →150:1→20:1)
washwashed with hexane

Sources & evidence

ORD record: ord-14643951f7534274956fe1913af07230
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855225B2

Reaction notes

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