alpha-(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)-N-methyl-o-toluamide → Mls003116016
Reaction equation
O[C:2]1([CH2:13][C:14]2[C:15]([C:20]([NH:22][CH3:23])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH3:12]>S(=O)(=O)(O)O>[CH3:12][N:3]1[C:2]2([CH2:13][C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20](=[O:21])[N:22]2[CH3:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 9.1 grams (0.0294 mole) of α-(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)-N-methyl-o-toluamide and 180 milliliters of 2 M sulfuric acid is refluxed for 20 hours. The mixture is cooled and the solid separated by filtration. The solid is then dissolved in methylene chloride and washed twice with water and once with brine. The organic phase is dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting oil is crystallized from ethanol to give 2,2'-dimethyl spiro[isoindolin-1,3'(4'H)-isoquinoline]1',3-dione, m.p. 202° - 203° C.