Ammonia → 4,5-Dihydro-1H-isoindole-1,3(2H)-dione
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[NH3:1].[C:2]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][O:4]1)=[O:3].C(OC(C)C)(C)C.C(OC)CCC>C(OCC)C.O1CCCC1>[CH2:8]1[CH:9]=[CH:10][C:11]2[C:2]([NH:1][C:5](=[O:4])[C:6]=2[CH2:7]1)=[O:3][NH3:1].[C:2]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][O:4]1)=[O:3].C(OC(C)C)(C)C.C(OC)CCC>C(OCC)C.O1CCCC1>[CH2:8]1[CH:9]=[CH:10][C:11]2[C:2]([NH:1][C:5](=[O:4])[C:6]=2[CH2:7]1)=[O:3]The 3-substituted phthalimidines of formula (I) wherein Z is OH can be prepared by reacting, under nondehydrating conditions, equivalent amounts of a 3-substituted phthalide of the formula ##STR3## wherein R, X, Y, a and b have the same meanings as above, and ammonia, or a primary aliphatic or aromatic amine. The reaction is preferably carried out in the presence of an inert organic solvent for the phthalide such as tetrahydrofuran, diethyl ether, diisopropyl ether, methyl n-butyl ether and the like. The solvent should have a boiling point below about 100° C. to permit ready separation from the reaction product by distillation at moderate temperatures. This serves to minimize dehydration of the 3-hydroxy group on the phthalimidine product. The primary amines employed in the reaction are those of the formula H2N--Q where Q has the same meaning as above. When the reaction is conducted at temperatures above about 100° C., dehydration takes place to produce a 3-substituted phthalimidine of formula (II).
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