Hydrochloric Acid → 1-Oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13]C)=[O:12])=[CH:8][CH:9]=2)[CH2:4][NH:3]1.C1COCC1.O.[OH-].[Li+].Cl>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][NH:3]1Participants
Conditions
- Temperature
- 23 °C
Procedure
To a 100 mL round bottom flask containing methyl 1-oxoisoindoline-5-carboxylate (200 mg, 1.046 mmol) was added THF (6 mL) and H2O (2 mL) the mixture was stirred at 23° C. for 2 min. At this time, lithium hydroxide monohydrate (87 μL, 3.14 mmol) was added and the flask was gently heated on aluminum block for 5 min. The solid went into solution and LC/MS showed product formation. The contents of the reaction were poured into HCl (1 M, 15 mL) and extracted with DCM (15 mL). An emulsion formed, the layers separated, and a white solid formed at the boundary of the layers and stuck to the separatory funnel. This material was collected, dissolved in MeOH, and concentrated. After drying under high vacuum for 2 h, the 1-oxoisoindoline-5-carboxylic acid thus obtained was taken on directly to the next reaction without further purification.
Workup
- temperaturethe flask was gently heated on aluminum block for 5 min
- extractionextracted with DCM (15 mL)
- customAn emulsion formed
- customthe layers separated
- customa white solid formed at the boundary of the layers
- customThis material was collected
- dissolutiondissolved in MeOH
- concentrationconcentrated
- customAfter drying under high vacuum for 2 h
Sources & evidence
- ORD record
- ord-8e2647b000154c8799f46eb4f3e6755e
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096527B2
Reaction notes
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