Sodium Hydroxide → {3-Chloro-4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([O:32]CC)=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][CH3:20])=[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]3=[C:11]([O:25][CH:26]([F:28])[F:27])[C:10]=2[CH2:9]1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][CH3:20])=[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]3=[C:11]([O:25][CH:26]([F:28])[F:27])[C:10]=2[CH2:9]1Participants
4
Procedure
Ethyl {3-chloro-4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate (0.141 g, 0.288 mmol) was heated to reflux in a 1:1 mixture of 2N sodium hydroxide:ethanol (6 ml) for 1.5 hours. The reaction was cooled to room temperature. The ethanol was evaporated and the mixture acidified with 2N aqueous hydrochloric acid. The resulting white solid was collected by filtration, washed with water and dried under vacuum to give the title compound (0.125 g, 0.271 mmol). LC/MS: Rt=3.19, [MH]+ 462.