Hydrochloric Acid → {4-[4,9-Bis(ethyloxy)-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetic acid
Reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][C:15]=3[F:26])[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][CH3:30])=[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=12)[CH3:2].Cl>C(O)(=O)C>[CH2:29]([O:28][C:7]1[C:8]2[C:9](=[O:27])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=3[F:26])[C:11](=[O:13])[C:12]=2[C:4]([O:3][CH2:1][CH3:2])=[C:5]2[CH:34]=[CH:33][CH:32]=[CH:31][C:6]=12)[CH3:30]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Ethyl {4-[4,9-bis(ethyloxy)-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate (0.050 g, 0.11 mmol) was dissolved in glacial acetic acid (2 ml) and 2N hydrochloric acid (2 ml) added which caused precipitation. The reaction mixture was heated to 100° C. under argon (the precipitate went back into solution) for 2 hours. The reaction mixture was cooled to room temperature and water added with stirring for 5 minutes. A solid precipitate formed which was filtered, washed with water, and collected to give the title compound as a yellow solid. The product was dried overnight in a vacuum oven (0.024 g, 0.05 mmol).
Workup
- customprecipitation
- customfor 2 hours
- temperatureThe reaction mixture was cooled to room temperature
- additionwater added
- customA solid precipitate formed which
- filtrationwas filtered
- washwashed with water
- customcollected
Sources & evidence
- ORD record
- ord-896a0812e4f3421d9df5a06974942c6a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252833B2
Reaction notes
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