Hydrochloric Acid → 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid

HRID 451359Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[C:9]=2[CH3:17])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([OH:15])=[O:14])[C:9]=2[CH3:17])=[C:4]([C:18]([F:21])([F:19])[F:20])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylate (0.23 g, 0.77 mmol) in methanol (4.0 ml) was added 5N NaOH (3.0 ml) and the mixture was stirred at 80° C. for 2.0 h. The reaction mixture was cooled to room temperature and added 2N HCl (8.0 ml). The mixture was diluted with ethyl acetate and washed with water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (1:1 to 1:9 hexane:ethyl acetate) to give the title compound (211 mg, 96%) as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated on a rotary evaporator
customThe resulting residue was purified by silica-gel column chromatography (1:1 to 1:9 hexane:ethyl acetate)

Sources & evidence

ORD record: ord-f8e9b324c9ad494d82a786838f468ac2
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487117B2

Reaction notes

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