Ethanol → 5-Ethyl-2-(2'-fluoro-4'-methyl-3'-trifluoromethylanilino)phenylacetic acid

HRID 2044204Notes

Reaction equation

CN(C)[C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[CH:8]=[CH:7][C:6]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[C:15]=1[F:25].CC[OH:30]>[OH-].[Na+]>[CH2:11]([C:9]1[CH:8]=[CH:7][C:6]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[C:15]=2[F:25])=[C:5]([CH2:4][C:3]([OH:26])=[O:30])[CH:10]=1)[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of the above 5-ethyl-2-(2′-fluoro-4′-methyl-3′-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide described in Example 3 (0.9 g, 2.4 mmol) in EtOH (25 mL) and 4N NaOH (12 mL) is heated to 80° C. overnight. After cooling, the reaction is concentrated under reduced pressure and diluted with ice cold EtOAc. The pH of the aqueous layer is adjusted to 1-2 with ice cold 2.5 N HCl. The separated organic layer is dried with Na2SO4 and concentrated to a solid. The solid is purified by trituration with an Et2O/hexane mixture to give the title acid, 5-ethyl-2-(2′-fluoro-4′-methyl-3′-trifluoromethylanilino)phenylacetic acid.

Workup

temperatureAfter cooling
concentrationthe reaction is concentrated under reduced pressure
additiondiluted with ice cold EtOAc
dry with materialThe separated organic layer is dried with Na2SO4
concentrationconcentrated to a solid
customThe solid is purified by trituration with an Et2O/hexane mixture

Sources & evidence

ORD record: ord-28a8aea2b7184a28abf32d2b96c0a729
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586782B2

Reaction notes

Loading…