Anthranilic acid, methyl ester

Indazoles can be considered as either azaindoles or azaisoindoles depending on the reader s prejudice. Benzydamine (54) represents a drug with this heterocyclic nucleus. Alkylation of the amine of anthranilic acid methyl ester with benzyl chloride in the presence of sodium acetate gives 52. Treatment with nitrous acid leads to the nitrosoamine, which cyclizes spontaneously to the 3-ketoindazole system, 53. This intermediate forms an ether of its enol form on heating the sodium salt with 3-dimethylaminopropyl chloride. There is thus obtained benzydamine (54), a fairly potent nonsteroidal antiinflammatory agent with significant antipyretic and analgesic properties. 

V-methyl-7V-(o-aminophenyl)anthranilic acid methyl ester... 

To a solution of 175 g of anthranilic acid methyl ester in 2 L of water and 120 ml of concentrated hydrochloric acid at 25°C was added concentrated solution of 80 g sodium nitrite. The product was dissolved in solution of 500 g NaOH in 1.5 L of water. To this solution under nitrogen was added 400 g of sodium bisulfite. The mixture was stirred for 6 hours at 75°C under nitrogen. The obtained solid product was dissolved in water and then to the solution was added 750 ml glacial acetic acid. The yield of l-benzyl-3-(3-(dimethylamino) propoxy)-lH-indazole 70%, M.P. 154-156°C. 

P.22) Benzoic acid, 2-amino-, methyl ester, methyl anthranilate, methyl 2-aminobenzoate, anthranilic acid methyl ester [134-20-3] FEMA 2682... 

Euxylophoricine F (90) exhibits the same uv spectrum as the other euxylophoricines. Methylation with methyl iodide and potassium carbonate yields Ni3-methyleuxylophoricine A, indicating that euxylophoricine F is a 2,3-disubstituted rutaecarpine derivative. The structure was confirmed by synthesis. Condensation of 4-benzyloxy-5-methoxy-anthranilic acid methyl ester with 1,2,3,4-tetrahydro-l-keto-p-carboline in the presence of phosphorus oxychloride and subsequent hydrogenolysis gave (90). 

Anthranilic acid methyl ester. See Methyl anthranilate... 

Hydroxycitronellal DMA. See Hydroxycitronellal dimethyl acetal Hydroxycitronellal methyl anthranilate CAS 89-43-0 EINECS/ELINCS 201-908-1 Synonyms Aurantiol Aurantium Hydroxycitronellylidene methyl anthranilate N-(7-Hydroxy-3,7-dimethyloctylidene) anthranilic acid methyl ester Methyl anthranilate hydroxycitronellal Methyl N-3,7-dimethyl-7-hydroxyoctylidenanthranilate Methyl 2-((7-hydroxy-3,7-dimethyloctylidene) amino) benzoate... 

N-(7-Hydroxy-3,7-dimethyloctylidene) anthranilic acid methyl ester. See Hydroxycitronellal methyl anthranilate... 

Synonyms 2-Aminobenzoic acid methyl ester o-Aminobenzoic acid methyl ester Anthranilic acid methyl ester Benzoic acid, 2-amino-, methyl ester 2-Carbomethoxyaniline o-Carbomethoxyaniline 2-(Methoxycarbonyl) aniline Methyl 2-ami nobenzoate Methyl-o-aminobenzoate Methyl 2-anthranilate Neroli oil, artificial... 

SYNS o-AMINOBENZOIC ACID METHYL ESTER 2-AMINOBENZOIC ACID METHYL ESTER o-CARBOMETHOXYANILINE 2-CARBOMETHO-XYANILINE FEMA No. 2682 2-(METHOXY-CARBONYL)ANILINE METHYL o-AIvIINOBENZO-ATE METHYL 2-AMINOBENZOATE METHYL ANTHRANILATE (FCC) METHYLESTER KYSELINY ANTHRANILOVE NEROLI OIL, ARTIFICAL... 

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... 

Methyl Anthranilate.—The methyl ester of anthranilic acid, methyl... 

Anisic acid, methyl ester [Benzoic acid, 4-methoxy-, methyl ester], 55,40,41 o-Anisidine (Benzenamine, 2-raethoxy-], p-bromination of, 55,23 [10]ANNULENE,[11-Oxabicyclo[4.4.1]-undeca-l,3,5,7,9-pentaene], 55, 86 Anthranilic acid [Benzoic acid, 2-amino-], p-bromination of, 55, 23 Apparatus, distillation of benzocyclopro-pene for, 55,13... 

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... 

Esterification. The formation of an ester from an acid (or its derivative) and an alcohol is of limited appHcation siace carboxyUc esters are comparatively rare substitueats ia dyes. Esters of A/-(3-hydroxyethylaniLiaes are important iatermediates for azo disperse dyes for polyester. Another example is methyl anthranilate, formed by the classical esterification of anthranilic acid usiag methanol and sulfuric acid. 

Methyl Anthranilate.—This ester is one of extreme importance, and to it is largely due the possibility of manufacturing artificial neroli oils. It was discovered as a constituent of neroli oil in 1895 by Walbaum, and has since been identified in numerous other flower oils, such as tuberose, ylang-ylang, jasmin, and gardenia. Its value in synthetic perfumery is therefore obvious. Its constitution is that of a methyl ester or orthp-amido-benzoic acid, of the formula here shown —... 

Anthranilic acid, or o-amidobenzoic acid, C H (NH2)(COOH),. is the-acid constituent of the ester found in neroli, petit-grain, jasmin, and mandarin oils. It is a solid crystalline substance melting at 145°. It is prepared artificially, and then converted into synthetic methyl anthranilate.. To prepare anthranilic acid, o-nitrobenzaldehyde is reduced by tin and hydrochloric acid to anthranil,... 

At a finer level of resolution, compounds with similar hydrocarbon skeletons may vary in functional group, degree of unsaturation, or oxidative state. For example, the volatile methyl esters of benzoic, salicylic and anthranilic acids (1 Fig. 5.1) differ only in -position functionality, but they are olfactorily distinct to humans and at least to some phytophagous insects (Raguso et al, 1996 Maekawa et al., 1999). Furthermore, many scent compounds have positional isomers and enantiomers that elicit different behavioral responses from flower visitors (Williams and Whitten, 1983 Hick et al, 1999). The refinement of capillary gas chromatography-mass... 

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. 

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