76746-92-4Relevant articles and documents
Isoquinolones: Part IV - Synthesis of 3-Methylisoquinolone-4-carboxylic Acids and Action of Ammonia and Aqueous Methyl Amine on 3-Methylisocoumarin-4-carboxylic Acid Esters
Datta, D.,Tirodkar, R. B.,Usgaonkar, R. N.
, p. 641 - 643 (2007/10/02)
Ammonia reacts with 3-methylisocoumarin-4-carboxylic acid ester (II) on a boiling water-bath to give homophthalimide (III, R'=H) and 3-methylisoquinolone-4-carboxylic acid ester (IV) in nearly equal amounts.At room temperature ammonia reacts to give IV as the major product in good yield.Aq. methyl amine, however, reacts with II to give N-methylhomophthalimide (III, R'=Me) as the major product along with small amounts of compound VI (R1=Me) and some unchanged isocoumarin.Formation of the various products has been rationalised.