Water → HCID 54145680, compound

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Reaction Steps

The process for preparing this compound will be described below, along with its physical properties. A solution of 5.6 grams of isoindoline in 50 milliliters of benzene is added dropwise to a solution of 4.7 grams of 4-ethoxycarbonyloxy-3-methoxy-cinnamyl chloride in 30 milliliters of benzene, after which the mixture is stirred for 1 hour at room temperature and then for 2 hours at 60° C. After completion of the reaction, water is added to the reaction mixture and extracted with benzene followed by distilling the solvent off to obtain an oily product, which is dissolved in a solution of 0.95 gram of potassium hydroxide in 50 milliliters of methanol and stirred for 30 minutes at room temperature. The reaction solution is then concentrated to dryness, and a 5% aqueous sodium hydroxide solution is added to the residue to precipitate crystals, which are filtered off. After adding an excess of ammonium chloride to the mother liquor, it is extracted with chloroform. The oily product obtained after distilling off the chloroform is transformed to a maleic acid salt by operating as in Example 15, which then is recrystallized from methanol to obtain 3.5 grams (yield 56.8%) of N-(4-hydroxy-3-methoxycinnamyl)-isoindoline.maleic acid salt as crystals having a melting point of 162°-164° C. (decomposition).

Provenance & Evidence