Sodium Chloride → 7-Hydroxy-2,3-dimethyl-2,3-dihydro-isoindol-1-one
Reaction equation
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH:7]2[CH3:13].N([O-])=[O:15].[Na+].[Na+].[Cl-]>OS(O)(=O)=O>[OH:15][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH:7]2[CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
7-amino-2,3-dimethyl-2,3-dihydro-isoindol-1-one (11.45 g) is suspended in a mixture of ice (27 g) and H2SO4 conc. (9.70 mL) and cooled to −10° C. Aqueous sodium nitrite solution (2.5 molar, 31.18 mL) is added dropwise, so that the temperature does not rise above 0° C. and the solution is stirred for 15 min at this temperature. Then H20 (135 mL) is added and the solution is heated to 80° C. for 15 min. For working up it is combined with 10% NaCl solution (100 mL) and extracted twice with 100 mL of CH2Cl2. The organic phase is extracted with NaOH solution (0.2 molar) and then the aqueous phase is acidified (HCl aq. conc.) and re-extracted with CH2Cl2. The organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo.
Workup
- customdoes not rise above 0° C.
- additionThen H20 (135 mL) is added
- temperaturethe solution is heated to 80° C. for 15 min
- extractionextracted twice with 100 mL of CH2Cl2
- extractionThe organic phase is extracted with NaOH solution (0.2 molar)
- extractionre-extracted with CH2Cl2
- customThe organic phase is dried on magnesium sulphate
- filtrationfiltered off from the desiccant and the solvent
Sources & evidence
- ORD record
- ord-eb66decfd7a04dac9da722a737a8a581
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846689B2
Reaction notes
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