108890-73-9Relevant articles and documents
Oxidative Cleavage of C2-C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates
Kalbandhe, Amit H.,Kavale, Ashish C.,Thorat, Prerana B.,Karade, Nandkishor N.
supporting information, p. 763 - 768 (2016/03/12)
On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.
Beyond conventional routes, an unprecedented metal-free chemoselective synthesis of anthranilate esters via a multicomponent reaction (MCR) strategy
Sarkar, Satavisha,Khan, Abu T.
supporting information, p. 12673 - 12676 (2015/08/06)
A hitherto unreported route for the synthesis of anthranilate esters is demonstrated using 2-nitrobenzaldehyde, malonitrile and an alcohol or amine via a metal and oxidant free multicomponent reaction (MCR) strategy. This process simultaneously installs an ester and urea or urethane functionality via CO and CN bond formations via concurrent oxidation of the aldehyde group and reduction of the nitro group involving an intramolecular redox process.
Reinvestigation of the synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) via 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) or dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1)
Fakhraian, Hossein,Heydary, Mehdi
, p. 151 - 156 (2014/02/14)
The synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) using respectively equimolar amounts of 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) with 4-(parafluorobenzoyl)piperidine (3) and dihydro-5H-oxazole(2,3-b) quinazolin-5-one (1) with hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) is reinvestigated. The one-pot reaction of ethyl-2-aminobenzoate with ethyl chloroformate and ethanol amine has afforded 3-(2-chloroethyl)-2,4-(1H,3H) -quinazolinedione (2) (86%) that was then refluxed with 4-(parafluorobenzoyl) piperidine (3) in ethyl methyl ketone in the presence of sodium carbonate to obtain free base of ketanserin (87%). In another attempt, a very pure hydrochloride salt of ketanserin (5.HCl) was synthesized using equimolar amounts of dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1) and hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) by a solvent-less fusion method. Thus, under optimized conditions, 180°C and a reaction time of 30 min, the powder mixture was transformed into glassy crystals that were initially readily soluble in chloroform but were transformed afterwards over time (2 h) to white precipitates (5.HCl) suspended in chloroform with a yield of 72%.
