Acetylanthranilic acid

A-Acetylanthranilic acid [89-52-1] M 179.1, m 182-184 , 185-186 , 190 (dec), pK 3.61. Wash with distilled H2O and recrystallise from aqueous AcOH, dry and recrystallise again from EtOAc. Also recryst from water or EtOH. [J Chem Soc 2495 7957 J Am Chem Soc ll 6698 7955.]... 

Preparation of Intermediate Compound 4-Chloro-5-Sulfamyl-N-Acetylanthranilic Acid To a hot solution (80°C) of 366 g (1.482 mols) of magnesium sulfate (Epsom salts) in 2.8 liters of water was added 130 g (0.495 mol) of powdered 5-chloro-2-methyl-4-sulfamyl-acetanilide. With stirring and maintaining the temperature at 83°C, 234 g (1.482 mols) of potassium permanganate was added portionwise over a period of 2 hours. The mixture was then kept at 85°C with stirring for an additional 3 hours. By this time the pink color of the permanganate had been discharged. 

Preparation of Intermediate Compound 2-Methyl-3-o-Tolyl-6-Sulfamyl-7-Chloro-4(3H)-Quinazoiinone Set up a 5-liter 3-necked flask fitted with a stirrer, condenser and a drying tube. To a stirred mixture of 100 g (0.342 mol) of powdered 4-chloro-5-sulfamyl-N-acetylanthranilic acid, 40.2 g (0.376 mol) of o-toluidine and 2.0 liters of dry toluene was added dropwise, over a period of 15 minutes, 21.7 ml (34.1 g) (0.248 mol) of phosphorus trichloride. The mixture was then refluxed for 10 hours. The solid turned somewhat gummy towards the latter part of the first hour. The mixture then became more free flowing as heating was continued. Let stand overnight. The yellow solid was filtered, washed with toluene and dried. The toluene filtrate was discarded. The dried solid was triturated with 1.5 liters of 10% sodium bicarbonate, filtered and the cake washed with water. The filtrate on acidification yielded 11.5 g of the starting acid. The damp product was dissolved in 4,5 liters of 95% ethanol and the solution treated with charcoal and filtered. On cooling filtrate yielded 69.5 g (55.5%) of the title compound, MP 271.5° to 274°C. 

Quinaldine (2-methyl-quinoline) (2) 2-methyl-4(lH)-quinolinone (3) 3 -hydroxy-2-methyl-4( 1 H)quinolinone (4) N-acetylanthranilic acid (5) Anthranilic acid (6) Catechol (1) Quinoline (2) 2(lH)quinolinone (3) 8-hydroxy-2(lH)quinolinone (4) 8-hydroxycoumarin (5) 2, 3-dihydroxyphenylpropionic acid... 

Acetylacetanilid, a24 Acetyl acetate, a22 Acetylacetone, p34 A-Acetylanthranilic acid, all Acetylbenzene, a31 Acetylcyclopropane, c410 Acetylene dichloride, d228, d229... 

Acetic Anhydride Acetone Dicarboxylic Acid N-Acetylanthranilic Acid N-Acetylmescaline Aluminum Foil ( ) Ammonium Acetate Anthranilic Acid Barbituric Acid Benzaldehyde Benzocaine... 

This indoline derivative has antihypertensive and diuretic actions. Indapamide (233) in methanol under nitrogen was irradiated with a medium-pressure mercury lamp through a copper sulphate filter solution for 12 h. The filter removed wavelengths below 300 nm. Products were separated by preparative TLC and identified as 2-methylindoline (234), the formylhydrazide (235), the amide (237) and semicarbazide. The procedure was repeated under oxygen to give the above products plus the urethane (236), acid (238), ester (239) and TV-acetylanthranilic acid [146]. 

Japan A -acetylanthranilic acid, ephedrine, ergometrine, ergotamine, isosafrole, lysergic acid, 3,4-methylenedioxyphenyl-2-propanone, l-phenyl-2-propanone, piperonal, pseudoephedrine and safrole 17 December 1999... 

Acetylacetaldehyde dimethyl acetal, d435 Acetylacetone, p31 N- Acetylanthranilic acid, al 1 Acetylbenzene, a31 Acetylcyclopropane, c368 Acetylene dichlorides, d 79, dl80... 

Reagents i, JV-Acetylanthranilic acid, P0C13 ii, LiOH iii, T1(NOj)3, H20, MeCN, DMF iv, Se02, AcOH, heat... 

Acetic anhydride TV-Acetylanthranilic acid Ephedrine Ergometrine Ergotamine Isosafrole Lysergic acid 3,4-Methylenedioxyphenyl-2-propanone Norephedrine l-Phenyl-2-propanone Piperonal Potassium permanganate Pseudoephedrine Safrole Acetone Anthranilic acid Ethyl ether Eiydrochloric acid3 Methyl ethyl ketone Phenylacetic acid Piperidine Sulphuric acid3 Toluene... 

Hydroiodic Acid (57%) Isosafrole Methylamine N-Acetylanthranilic Acid N-Methylephedrine... 

V-acetylanthranilic acid. (o-acetylamino-benzoic acid). CH3CONHC6H4COOH. 

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