Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/18034
Title: Synthesis of a novel water soluble phthalimide derivative of acetaminophen as potential analgesic and antipyretic agent
Authors: Reddy, Y Dathu
Kumari, Y Bharathi
Dubey, P K
Keywords: Phthalic anhydride;Phthalimide;4-amino phenol;Acetaminophen;Analgesic;Anti pyretic
Issue Date: May-2013
Publisher: NISCAIR-CSIR, India
Abstract: A short process for the preparation of water soluble, potential analgesic compound, N-[(4-hydroxy-phenylcarbamoyl)-methyl]-phthalamic acid 4 has been developed. Two synthetic routes (A and B) have been established for the preparation of 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-(4-hydroxyphenyl)acetamide 3. In route A, 4-aminophenol 5 is reacted with chloroacetyl chloride 6 in solution of potassium acetate and acetic acid at 0-5°C to yield N-(4-hydroxyphenyl)-2-chloroacetamide 7. The latter is reacted with potassium phthalimide 8 and KI in DMF at 130°C to give 3. Alternatively, in route B, reaction of phthalic anhydride 8 with glycine 9 at 150°C yields the acid intermediate (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid 11, which on reaction with 4-aminophenol 6 in DMF and in the presence of dicyclo­hexylcarbodimide gives 3. The latter is hydrolysed in ethanolic KOH to afford 4.
Page(s): 691-693
URI: http://hdl.handle.net/123456789/18034
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.52B(05) [May 2013]

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