Ethanol → [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid
Reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=3)[C:9](=[O:25])[C:8]=2[C:7]([O:26][CH2:27][CH3:28])=[C:6]2[CH:29]=[CH:30][CH:31]=[CH:32][C:5]=12)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(O)C>O>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=3)[C:9](=[O:25])[C:8]=2[C:7]([O:26][CH2:27][CH3:28])=[C:6]2[CH:29]=[CH:30][CH:31]=[CH:32][C:5]=12)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl [4-(4,9diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (5.86 g, 13.5 mmol) and potassium carbonate (12 g) were added td a mixture of ethanol (146 ml) and water (70 ml) and heated to reflux for 2 h. The solution was cooled to room temperature and the solvent evaporated under vacuum to leave an off-white solid. The solid was slurried in water and the water was evaporated under vacuum. The residue was stirred in hydrochloric acid (2N) for 2 h, filtered and washed with water. Drying of the solid at 40° C. in a vacuum oven gave the title compound as a white solid (4.5 g, 82%)
Workup
- temperatureheated
- temperatureto reflux for 2 h
- customthe solvent evaporated under vacuum
- customto leave an off-white solid
- customthe water was evaporated under vacuum
- filtrationfiltered
- washwashed with water
- customDrying of the solid at 40° C. in a vacuum oven
Sources & evidence
- ORD record
- ord-d9b89b41628149ef84f17ce92abe2205
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173047B2
Reaction notes
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