Isatoic acid anhydride

Some isatoic acid anhydrides are readily hydrolyzed during oxidation so that the corresponding A -(2-hydroxyphenyl)oxamidic acids are isolated as products [260], With 7-chloroisatin, treatment with 30% hydrogen peroxide in 5% aqueous sodium hydroxide for 40 min at 65 °C produces chloroanthranilic acid in 78% yield (equation 395) [1168]. 

Isatoic acid anhydride. See Isatoic anhydride Isatoic anhydride... 

CAS 118-48-9 EINECS/ELINCS 204-255-0 Synonyms Anthranilic acid N-carboxylic acid anhydride 1H-Benzo[D][1,3] oxazine-2,4-dione 2H-3,1-Benzoxazine-2,4(1H)-dione lA Isatoic acid anhydride... 

Oxidation of isatin. Two products are possible from Baeyer-Villiger oxidation of isatin (1). Oxidation with K2S208 in sulfuric acid gives only the 1,4-beiuoxazine 2, whereas oxidation with H202-H0Ac gives the anhydride (3) of isatoic acid.1 An earlier preparation of compounds of type 2 involves reaction of o-aminophenols and oxalyl chloride.2... 

Beilstein Handbook Reference) AI3-24983 Benzoic acid, 2-(carboxyamino)-, cyclic anhydride BRN 0136786 N-Carboxyanthranilic acid cyclic anhydride N-Carboxyanthranilic anhydride EINECS 204-2660 HSDB 5017 Isatoic acid anhydrtde Isatoic anhydride NSC 104662. 

Fig. 2. Synthesis of uma2enil (18). The isonitrosoacetanihde is synthesized from 4-f1iioroani1ine. Cyclization using sulfuric acid is followed by oxidization using peracetic acid to the isatoic anhydride. Reaction of sarcosine in DMF and acetic acid leads to the benzodiazepine-2,5-dione. Deprotonation, phosphorylation, and subsequent reaction with diethyl malonate leads to the diester. After selective hydrolysis and decarboxylation the resulting monoester is nitrosated and catalyticaHy hydrogenated to the aminoester. Introduction of the final carbon atom is accompHshed by reaction of triethyl orthoformate to...

These formulae explain the scission products of the two alkaloids and the conversion of evodiamine into rutaecarpine, and were accepted by Asahina. A partial synthesis of rutaecarpine was effected by Asahina, Irie and Ohta, who prepared the o-nitrobenzoyl derivative of 3-)3-amino-ethylindole-2-carboxylic acid, and reduced this to the corresponding amine (partial formula I), which on warming with phosphorus oxychloride in carbon tetrachloride solution furnished rutaecarpine. This synthesis was completed in 1928 by the same authors by the preparation of 3-)S-amino-ethylindole-2-carboxylic acid by the action of alcoholic potassium hydroxide on 2-keto-2 3 4 5-tetrahydro-3-carboline. An equally simple synthesis was effected almost simultaneously by Asahina, Manske and Robinson, who condensed methyl anthranilate with 2-keto-2 3 4 5-tetrahydro-3-carboline (for notation, see p. 492) by the use of phosphorus trichloride (see partial formulae II). Ohta has also synthesised rutaecarpine by heating a mixture of 2-keto-2 3 4 5-tetrahydrocarboline with isatoic anhydride at 195° for 20 minutes. 

The substance represented by formula (IV), viz., 4-hydroxy-3-allyl-3 4-dihydroqviinazoline, m.p. 130°, was synthesised by Reynolds and Robinson, and proved to be different from vasicine. Spath and Kuffner established the identity of the degradation product (V), upon which formula (IV) for vasicine was chiefly based by synthesis from isatoic anhydride, which, on treatment with glycine ester hydrochloride and sodium meth-oxide, gave the substituted Wppuric acid (VI), and this, on heating with... 

It was found inadvisable to use more than four molecules of form-amide [ (47) when R = H] per molecule of anthranilic acid and the condensation produces best results when the mixture is heated at 120 -130°C for 2 hr followed by further heating at 170°-180 C for 2 hr. Other variants of this reaction involve the use of ammonium o-acylaminobenzoates, anthranilic acid in the presence of nitriles and acetic anhydride, o-acetamidonitrile with acetic anhydride or hydrogen peroxide, anthranilic esters and aliphatic or aromatic amides or amidines, isatoic anhydride with amides or amidines, and anthranilic esters with aryl iminochlorides in acetoned The mechanism proposed by Bogert and Gotthelf has had experimental supporR and is represented in Scheme 12. 

As noted above, a convenient pathway to cinno-lines consists of intramolecular condensation of a diazonium group with a ketonic methyl group, or alternately with a double bond. The analogous reaction with an amide nitrogen leads to 1,2,3-benzotriazines, such as 198. Reaction of isatoic anhydride with N-aminomorpholine affords the hydrazide 196 then, treatment with nitrous acid yields initially the diazonium salt (197). Under the reaction conditions... 

One of the early steps in an allergic reaction consists in the release of a series of endogenous compounds referred to as mediators from sensitized cells. The finding in the early 1960s that cromolyn sodium, still the only approved drug of this class, blunts this reaction has led to an intense search for additional examples. It is of interest that a relatively simple anthranilic acid derivative has shown mediator-release inhibiting activity. Reaction of 3,4-dimethoxybenzalde-hyde (167) with isatoic anhydride 168 gives the condensation product 169, which, upon hydrolysis, affords tranilast (170) (43]. 

Isatin, a cyclic a-ketoamide, when reacted with potassium peroxydisulfate in the presence of sulfuric acid gave regioselectively an oxidized product, i.e. 2,3-dioxo-l,4-benzoxazine in almost quantitative yield under mUd conditions (equation 16). In contrast, when isatin reacted with 30% H2O2 in the presence of acetic acid and H2SO4, isatoic anhydride was obtained (equation 16) . ... 

The azathio isatoic anhydride 99 has been prepared by the reaction of 2-aminonicotinic acid 303 and thionyl chloride in ecu <2001JOC4413>, benzene, or cyclohexane as the solvent (Equation 40) <2004TL1377>. 

C8H9NO2, Mr 151.16, bp2w 135.5 °C, df 1.1682, ng 1.5815, occurs in a large number of blossom essential oils (e.g., neroli, ylang-ylang, and jasmin oils), grapes, and citrus oils. It occurs as white crystals mp 24-25 °C), or a yellowish liquid, that show blue fluorescence and have an orange blossom odor. Methyl anthranilate is prepared by esterification of anthranilic acid with methanol or by reaction of isatoic anhydride with methanol [163]. 

The use of activated anthranihc acid derivatives facUitates the preparation of the amides in those cases where the amines are either umeactive or difficult to obtain. Thus, reaction of (87-1) with phosgene gives the reactive the isatoic anhydride (89-1). Condensation of that with ortho-toluidine leads to the acylation product (89-2) formed with a simultaneous loss of carbon dioxide. This is then converted to the quinazolone (89-3) by heating with acetic anhydride. Reaction with sodium borohydride in the presence of aluminum chloride selectively reduces the double bond to yield the diuretic agent metolazone (89-4) [99]. 

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