N-methyl anthranilic acid

Evodia rutaecarpa (Juss.) Berth Wu Zhu Yu (Evodia) (fruit) Alkyl methyl quinolone alkaloids, evodiamine, limonin, evocarpine, rutaecarpine, N-methyl anthranilic acid, evodol, hydroxyevodiamine, N-methylanthranflamide, N,N-dimethyl-5 -methoxytryptamine, dehydroevodiamine.32,33,237 Antiemetic, analgesic, lower blood pressure, antibacterial. 

C]Tryptophan gave inactive alkaloids but tritiated 2,4-dihydroxy-quinoline (34) and its N-methyl derivative were incorporated into (47) (0.009 % and 0.020% respectively) an early route had suggested the derivation of what was essentially (34) from tryptophan. Radioisotope dilution showed the presence of both these quinoline precursors together with iV-acetyl- and N-methyl-anthranilic acid in A. baueri. A satisfactory incorporation of N-methylanthranilic acid into (47) was found in Evodia xanthoxyloides, and this, together with its natural occurrence, indicates that early methylation may be important in the biosynthesis of acridone alkaloids. 

Amino-2-hydroxy[4- C]butyric acid (the corresponding aldehyde has been condensed with o-aminobenzaldehyde to give vasicine 4-hydroxy-[2- C]glutamic acid (found with vasicine in Linaria yw/garis ), N-methyl-anthranilic acid, and N-formylanthranilic acid have been tested as vasicine precursors in A. vasica, without success. 

H-nmr 5 2.53 (3H, s, NMe) and 5.90 (IH, s, C3-H). The structure of (67) was partially revealed by alkaline hydrolysis which yields N-methyl-anthranilic acid and 3,4-dihydro-p-carboline. Boiling alcoholic potassium hydroxide degrades (67) to N-methylanthranilic acid, carbon dioxide and tryptamine. When boiled with alcoholic hydrochloric acid (67) yields optically inactive isoevodiamine [evodiamine hydrate (74)] which can be recyclized with acetic anhydride or oxalic acid to optically inactive evodiamine. (67) can be converted to rutaecarpine via the dry hydrochloride of (74), which, on heating, yields (63). The chemistry of evodiamine has been reviewed by Armarego (6) see also (25, 94, 134, 169). 

The biogenetic pathway proposed by Chakraborty for the formation of carbazole (1) and 3-methylcarbazole (2) proceeds through Af-phenylated anthranilic acid (406). This hypothesis is based on aromatic C-methylation of aniline with methionine, and originates from anthranilic acid (397) and prephenic acid (404). Until now, there are no N-phenylated anthranilic acid derivatives known naturally, therefore, this hypothesis is lacking substantial biogenetic evidence. However, the isolation of carbazole (1), 3-methylcarbazole (2), and several derivatives of 3-methylcarbazole... 

According to data in [190], the reaction of the anhydride 1 with 1-amino-2-mercapto-5-methyl-1,3,4-triazole takes place in an unusual manner it leads to the formation not of the corresponding anthranilamide but to the N-substituted anthranilic acid 306 (yield 62%), which is transformed into compound 307 with a yield of 57% when treated with phosphorus pentachloride or phosphorus oxychloride. 

Methylacetopyronone. See Dehydroacetic acid Methyl 12-acetoxy-9-octadecenoate Methyl 12-acetoxyoleate. See Methyl acetyl ricinoleate Methyl acetylacetate Methyl acetylacetonate. See Methyl acetoacetate Methyl acetylaminobenzoate CAS 2719-08-6 EINECS/ELINCS 220-318-5 Synonyms 2-(Acetylamino) benzoic acid, methyl ester Acetyl methyl anthranilate Acetyl-N-methyl anthranilate Methyl 2-(acetylamino) benzoate Methyl N-acetylanthranilate Empiricai C10H11NO3... 

Inspect the paper in ultraviolet light—conveniently in front on a Hanovia ultraviolet strip light—in a dark room. The acids show up as intense blue fluorescent spots. Mark with a pencil the positions of all spots. The position of the two spots arising from solution (C) should be compared with the single spots arising from solutions (A) and (B). It is probable that the solution (B) of pure N-methylan-thranilic acid may also reveal a faint spot corresponding to anthranilic acid still present in minute traces in the methylated acid cf. p. 223). 

The reaction is applicable to the preparation of amines from amides of aliphatic aromatic, aryl-aliphatic and heterocyclic acids. A further example is given in Section IV,170 in connexion with the preparation of anthranilic acid from phthal-imide. It may be mentioned that for aliphatic monoamides containing more than eight carbon atoms aqueous alkaline hypohalite gives poor yields of the amines. Good results are obtained by treatment of the amide (C > 8) in methanol with sodium methoxide and bromine, followed by hydrolysis of the resulting N-alkyl methyl carbamate ... 

N-(m-methylmercapto-phenyl)-aniline (MP 59° to 61°C) is prepared by condensing m-methyl-mercapto-aniline (BP 163° to 165°C/16 mm Hg) with the potassium salt of o-chloro-benzoic acid and decarboxylating the resultant N-(m-methylmercapto-phenyl)-anthranilic acid (MP 139° to 141°C) by heating, and then distilling. 

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... 

Because benzanilides exhibit fungicidal activity 38) and anthranilic acid esters have fungicidal and bactericidal activities 39,40), Kirino et al. attempted to derive a new class of fungicides from those having a hybrid structure, methyl N-(substituted benzoyl)anthranilates 41. Among various derivatives, m-substituted compounds (19) were shown to exhibit appreciable preventive activity against powdery mildew of cucumber. 

Tolfenamic acid is used as an injectable formulation in cattle and swine. In rats and target animals, tolfenamic acid is metabolized by hydroxylation either of the methyl or the methylchlorophenyl group producing two metabolites further oxidation of the hydroxymethyl group to the corresponding aldehyde or carboxylic acid can produce two additional metabolites. The two hydroxylated metabolites of tolfenamic acid, N-(2-hydroxymethyl-3-chlorophenyl)-anthranilic acid and N-(2-hydroxymethyl-3-chloro-4-hydroxyphenyl)-anthranilic acid, are much less potent than the parent compound in terms of anti-inflammatory and analgesic... 

Isatin (190) is a compound with interesting chemistry. It can be N- acetylated with acetic anhydride, N- methylated via its sodium or potassium salt and O- methylated via its silver salt. Oxidation of isatins with hydrogen peroxide in methanolic sodium methoxide yields methyl anthranilates (8lAG(E)882). In moist air, O-methylisatin (191) forms methylisatoid (192). Isatin forms normal carbonyl derivatives (193) with ketonic reagents such as hydroxylamine and phenylhydrazine and the reactive 3-carbonyl group also undergoes aldol condensation with active methylene compounds. Isatin forms a complex derivative, isamic acid (194), with ammonia (76JCS(pi)2004>. 

Most of the older methods of fluorimetric analysis of pesticides involved hydrolysis to form fluorescent anions. Co-ral (coumaphos) [147] was hydrolyzed in alkali to the hydroxybenzopyran, which was subsequently determined by means of its fluorescence. Guthion (azinphosmethyl) was hydrolyzed to anthranilic acid for fluorimetric analysis [148,149]. A method was developed [150] for Maretin (N-hydroxynaphthalimide diethyl phosphate) in fat and meat which involved hydrolysis in 0.5 M methanolic sodium hydroxide followed by determination of the fluorescence of the liberated naphthalimide moiety. Carbaryl (1-naphthyl N-methylcarbamate) and its metabolites have been determined by a number of workers using base hydrolysis and the fluorescence of the resulting naphtholate anion [151-153]. Nanogram quantities of the naphtholate anion could be detected. Zectran (4-dimethylamino-3,5-xylyl N-methylcarbamate) has been determined by the fluorescence of its hydrolysis product [154]. The fluorescence behaviour of other carbamate insecticides in neutral and basic media has been reported [155]. Gibberellin spray used on cherries has been determined fluorimetrically after treatment with strong acid [156]. Benomyl (methyl N-[l-(butylcarbamoyl)-2-benzimidazolyl]carbamate) has been analyzed by fluorimetry after hydrolysis to 2-aminobenzimidazole [157]. 

It is not possible to prepare biaryls containing a free carboxyl group directly by the diazo reaction. No biaryl is formed when (a) diazotized aniline and sodium benzoate, (b) diazotized anthranilic acid and aqueous sodium benzoate, or (c) diazotized anthranilic acid and benzene are used as components in the reaction.13 On the other hand, the reaction proceeds normally if methyl benzoate is used in reaction (a) or when methyl anthranilate replaces the anthranilic acid in (b) and in (c). The success of the diazohydroxide reaction appears to lie in the ability of the non-aqueous liquid to extract the reactive diazo compound from the aqueous layer.4 However, esters and nitriles can be prepared from esters of aromatic amino acids and cyanoanilines and also by coupling with esters of aromatic acids, and from the products the acids can be obtained by hydrolysis. By coupling N-nitrosoacetanilide with ethyl phthalate, ethyl 4-phenylphthalate (VIII) is formed in 37% yield. 

Dicarbonylimidazole reacted with the anthranilic acid derivative (498) to produce the fused isoxazolone IV-oxide (499) (77ZOR462). Methyl nitroacetate reacted with indole-3-carbaldehyde to produce (500) (70KGS1505). Treatment of (501) with base gave 3,4,5-triphenyl-2-isoxazoline N-oxide (Scheme 142) (69JOC984). The reaction was reported to be a direct displacement as (502) did not give a product and no incorporation of deuterium was found using DOMe. 

SYNS ANTHRANILIC ACID, N-(2-BENZYLID-ENEHEPTYLIDENE)-, METHYL ESTER METHYL N-(P-PENTYLCINNAMYLIDENE)ANTHRANILATE... 

SYNS ANTHRANILIC ACID, N-(3-(p-tert-BUTYLPHEN-YL)-2-METHYLPROPYLIDENE)-, METHYL ESTER BENZOIC ACID,2-((3-(4-(l,l-DIMETHYLETHYL)PHEN-YL)-2-METHYLPROPYLIDENE)AMINO)-, METHYL-ESTER METHYL-N-(p-tett-BUTYL-a-METHYLHYDRO-CINNAMYLIDENE) ANTHRANILATE VERDANTIOL... 

METHYL-o-ANISIDINE see MGO750 p-METHYL ANISOLE see MGPOOO 9-METHYLANTHRACENE see MGP750 METHYL ANTHRANILATE (FCQ see APJ250 N-METHYLANTHRANILIC ACID, METHYL ESTER see MGQ250... 

There are a few tetra- and pentacyclic analogues. Benzo analogues of 245 were prepared from pyridine-2,3-dicarboxylic acid anhydride and a tetralin derivative under conditions of the Friedel-Crafts reaction (85JCR(S)338). Pentacyclic compounds 258 (R = H or Me) were prepared from the bis adduct of anthranilic (or IV-methylanthranilic) acid to 1,4-benzoquinone, followed by cyclization in concentrated sulfuric acid (55JCS4440 66CB1991). 6-Methylquinoline-5,8-dione dimerized in the presence of ethanolic N-methyl-cyclohexylamine to 259 in very low yield and the dimerization is interpreted as two base-catalyzed addition reactions and three oxidation steps (71JCS(C)1253). 

The following compounds when heated with hydrochloric acid yield mercuric chloride and an organic acid The anhydride of o-hydroxy-mercuri benzoic acid and the anhydride of a-hydroxy mercuri- -hydroxy-j3-phenyipropionic acid, whilst o-chloromercuri benzoic methyl ester is decomposed by halogen acids, and cold dilute hydrochloric acid eliminates the acetoxymercuri group attached to the nitrogen in N-isodiacetoxymercuri anthranilic methyl ester. 

From the preceding N-iso-diacetoxy comj ound. 2-5 grams of the latter are suspended in 15 c.c, of methyl alcohol and 0 6 gram (1 nioL) of methyl anthranilate in 2 c.c. of acetic acid added, the whole being heated for thirty minutes on the water-bath. The mass is then allowed to stand for twenty-four hours in the ice-chest, filtered, and dried m vacuo over sulphuric acid. Yield 2-6 grams. 

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