4-Aminophthalhydrazide or isoluminol is a chemiluminescent compound that comprises a phthalazine ring. It is more hydrophilic than luminol. Isoluminol is commercially used in a wide variety of in vitro immunoassays and is a chemiluminescence amplifier for studying reactive oxygen species. It is also useful as an electroluminescence (ECL) biosensor and as a probe for rapid microbial detection.
The general procedure for the synthesis of 4-amino phthalazine hydrazide using 6-nitro-2,3-dihydrophthalazine-1,4-dione as starting material was as follows: Intermediate B was transferred to a 5L high-pressure hydrogenation reactor and 3 g of 10% palladium/carbon catalyst was added. The reaction system was heated to 35 ℃ and hydrogen was introduced until the pressure reached 4 atm, and the reaction was maintained at a constant pressure for 4 h. After the reaction was completed, the reaction was carried out with nitrogen. Upon completion of the reaction, the hydrogen in the reactor was replaced with nitrogen. Subsequently, the pH of the reaction solution was adjusted to 3-4 with 35% by weight concentrated hydrochloric acid. heating was continued to 100°C and the nitrogen gas flow was stopped. The reaction mixture was filtered while hot and the filtrate precipitated a large amount of solid after cooling to room temperature. The solid precipitate was collected by filtration and the filtrate could be used for organic solvent recovery. The resulting filter cake was washed with 400 ml of deionized water and dried to give 214 g of 4-amino phthalic hydrazide (isluminolide).
[1] Patent: CN106810501, 2017, A. Location in patent: Paragraph 0050
[2] Journal of the Chemical Society, 1937, p. 26,31
[3] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 471
[4] Bulet.Soc.Chim.Romania, 1930, vol. 12, p. 140,163
[5] Patent: CN105348202, 2016, A. Location in patent: Paragraph 0045; 0054; 0055; 0056
