Anthranilic acid methylation

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. 

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

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... 

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). 

This preparation illustrates the use of dimethyl sulphate to convert a primary amino group into the secondary monomethylamino group, without the methy-lation proceeding to the tertiary dimethylamino stage. The methylation of anthranilic acid is arrested at the monomethylamino stage by using i-i molecular equiN alents of sodium hydroxide and of dimethyl sulphate. The reactions can be considered as ... 

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 ... 

The valuable indicator methyl red (o-carboxybenzene-azo-dimethylaniline) is obtained by coupling diazotised anthranilic acid with dimethylaniline ... 

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. 

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 IV-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. 

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,... 

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. 

C 2Hi)jN2 22261-94-5) see Bamipine Thenalidine methyl 3-anilinopropionate (CioH, N02 21911-84-2) see lobenzamic acid methyl anthranilate... 

---