Sodium Hydroxide → HCID 67201188, compound
Reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]1[C:13]([O:15]CC)=[O:14])[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]1[C:13]([OH:15])=[O:14])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution of ethyl 2-ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxylate (0.283 g, 1.2 mmol) in ethanol (6 ml) and water (6 ml) was treated with 2M aqueous sodium hydroxide solution (0.6 ml) and stirred at 20° C. for 1.5 hrs. Starting material was still evident at this stage so a further aliquot of 2M aqueous sodium hydroxide solution (0.8 ml) was added and stirring continued for a further 4 hrs. The mixture was evaporated to remove the ethanol and the aqueous residue was diluted with water (40 ml), washed with diethyl ether (25 ml), then acidified to pH2 using 2M aqueous hydrogen chloride, and extracted with dichloromethane (4×25 ml). The organic extracts were combined, filtered through a hydrophobic frit, and evaporated to give 2-ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acid as a white solid (0.255 g) which was used without further purification.
Workup
- additionwas added
- stirringstirring
- waitcontinued for a further 4 hrs
- customThe mixture was evaporated
- customto remove the ethanol
- additionthe aqueous residue was diluted with water (40 ml)
- washwashed with diethyl ether (25 ml)
- extractionextracted with dichloromethane (4×25 ml)
- filtrationfiltered through a hydrophobic frit
- customevaporated
Sources & evidence
- ORD record
- ord-fc0ac82ac9834dda993a07c45464c881
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935832B2
Reaction notes
Loading…