C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:9][CH:8]=1)=O.[NH2:30]N.Cl>C(O)C>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:9][CH:8]=2)=[N:30]1A suspension of 21.2 g of (E)-2-[4-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenoxy]butyl]-1H-isoindole-1,3(2H)-dione (Example 48) in 300 ml of boiling ethanol is treated with 6 ml of anhydrous hydrazine. A suspension quickly develops, necessitating addition of 200 ml more ethanol to permit stirring. While stirring 35 ml of concentrated HCl is then added, the mixture refluxed a further hour, and filtered hot. The insolubles are washed with 200 ml of boiling water. The combined filtrates are taken to dryness in vacuo, leaving the hydrochloride salt of the title compound as shown by mass spectrometry. The product is utilized for synthesis without further purification.
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