Anthranilic acid, ethyl ester

Ethyl o-aminobenzoate. See Ethyl anthranilate Ethyl-p-aminobenzoate CAS 94-09-7 EINECS/ELINCS 202-303-5 Synonyms 4-Aminobenzoic acid ethyl ester p-Aminobenzoic acid ethyl ester Benzocaine Benzoic acid, 4-amino-, ethyl ester Benzoic acid, p-amino-, ethyl ester 4-Carbethoxyaniline 4-(Ethoxycarbonyl) aniline Ethylaminobenzoate Ethyl-4-aminobenzoate Ethyl p-aminophenylcarboxylate Ethyl PABA (INCI)... 

Selectivity of the FPD. The minimum detectable levels of four non-sulfur compounds, methyl anthranilate, pyridine, heptane and caproic acid ethyl ester, on the FPD at a signal/noise ratio of 2 were 368, 784.5, 759.8 and 760 ng, respectively. 

The benzoic acid derivative 457 is formed by the carbonylation of iodoben-zene in aqueous DMF (1 1) without using a phosphine ligand at room temperature and 1 atm[311]. As optimum conditions for the technical synthesis of the anthranilic acid derivative 458, it has been found that A-acetyl protection, which has a chelating effect, is important[312]. Phase-transfer catalysis is combined with the Pd-catalyzed carbonylation of halides[3l3]. Carbonylation of 1,1-dibromoalkenes in the presence of a phase-transfer catalyst gives the gem-inal dicarboxylic acid 459. Use of a polar solvent is important[314]. Interestingly, addition of trimethylsilyl chloride (2 equiv.) increased yield of the lactone 460 remarkabiy[3l5]. Formate esters as a CO source and NaOR are used for the carbonylation of aryl iodides under a nitrogen atmosphere without using CO[316]. Chlorobenzene coordinated by Cr(CO)j is carbonylated with ethyl formate[3l7]. 

Among the compounds commonly determined in research laboratories are diacetyl, 2,3-butandiol, glycerol, citramalic acid, amino acids (especially proline), histamine, ammonia, succinic acid, phosphate, ash, alkalinity of the ash, ethyl, acetate, methyl anthranilate, total volatile esters, higher alcohols (both total and individually) phenolic compounds, etc. An elegant method for determining ethyl esters, capronate, caprylate, caprinate, and laurate using carbon disulfide extraction and GLC has been published (123). 

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. 

Alkaloids of Delphinium dictyocarpum N- Acetyldelectine and Demethylenedelt-amine.—Further investigations of the aerial parts of D. dictyocarpum DC. have yielded a new base (34), C26H41N08, m.pt. 116—118 °C.27 Spectral analyses (i.r., n.m.r., and mass) indicate the presence of an N-ethyl and three methoxy-groups, and an N-acetyl anthranilate ester, on a lycoctonine-type skeleton. Saponification of (34) gave anthranilic acid and a base identical with that obtained from delectine (35). Therefore, this new alkaloid was assigned the structure of N-acetyldelectine (34). 

The ester is obtained in 97 per cent, yield by adding the methyl ester of methyl anthranilic acid to mercuric acetate solution in methyl alcohol, the reaction being complete in about thirty minutes. It forms fine needles, M.pt. 200° C., easily soluble in chloroform, hot acetic acid, boiling alcohols, ethyl acetate, acetone, or benzol, slightly soluble in cold water. 

In a modern procedure anthranilic acid is diazotized in dilute sulfuric acid and the filtered solution is added to potassium iodide, also in the dilute acid. The crude brown acid (92%) is converted into the ethyl ester, b.p. 150-151°/13 mm. (71%), which on hydrolysis with ethanolic potassium hydroxide gives the pure acid, m.p. 163°, in almost theoretical yield. 

A further solution to the problem of isomer formation in the synthesis of oxoacridine carboaylic acids is to mask one of the two carboxyl groups. The requisite 2-(2-metho carbonylphet lamino)benzoic acids are available from methyl anthranilates reaction with diphenyliodonium carboxylates. The esters which result after cyclisation with polyphosphoric ethyl ester undergo ready alkaline l drolysis to the acid (G.W. Rewcastle and W.A. Denny. Synthesis. 1985. 220). 

Similarly, 3-amino-4(3//)-quinazolinones (600) are formed in high yields when methyl or ethyl o-acylaminobenzoates are heated with hydrazine in an alcohol. Alternatively, acylation and cyclization of an o-aminobenzoylhydrazine is effected by heating with anhydrous formic acid, ethyl orthoformate, or acetic anhydride. Related is the action of heat on a mixture of anthranilic esters and semicarbazides to yield A3-aminated 2,4(1//,3//)-quinazolinediones (601). Reactions which involve... 

Higher amides, as well as the nitriles, are poorly represented as reagents for converting o-amino esters to annelated pyrimidines. At least methyl anthranilate and ethyl cyanoformate (not usually a reactive chemical) formed a good yield of 2-ethoxycarbonylquinazolin-4-one (140) when heated at 120°C with hydrogen chloride in acetic acid.325... 

Bomyl butyrate Bornyl formate Bomyl isovalerate Bornyl valerate p-Bourbonene 2-Butanol Butan-3-one-2-yl butyrate Butter acids Butter esters n-Butyl acetate Butyl acetoacetate Butyl alcohol n-Butylamine Butyl anthranilate Butyl butyrate Butyl butyryl lactate a-Butylcinnamaldehyde Butyl cinnamate Butyl 2-decenoate Butyl ethyl malonate... 

Phenylalanine hydroxylase occurs only in mammalian liver (that is, in the rat, guinea-pig, rabbit, d<, chicken, and human) (see also 259). No activity has been observed in (rat) lung, kidney, brain, or muscle. The system is quite speciOc for L-phenylalanine. Tjrro-sine is not formed from n-phenylalanine, nor are the corresponding p-phenols formed from N-acetyl- or N-chloroacetyl-L-phenylalanine, L-phenylalanine ethyl ester, DL-phenylglycine, phenylserine, phenylpyruvic acid, phenylethylamine, benzoic acid, hippuric acid, cinnamic acid, or mandelic acid (768), or from aniline, acetanilide, tryptophan, kynurenine, anthranilic acid, or phenylacetate (557). This specificity is a distinguishing character of the enzyme, which occurs in the same tissue as the nonspecific aromatic hydroxylase described above. 

Amyl, butyl, and iso-propyl acetates are all made from acetic acid and the appropriate alcohols. All are useful lacquer solvents and their slow rate of evaporation (compared to acetone or ethyl acetate) prevents the surface of the drying lacquer from falling below the dew point, which would cause condensation on the film and a mottled surface appearance (blushing). Other esters of importance are used in perfumery and in plasticizers and include methyl salicylate, methyl anthranilate, diethyl-phthalate, dibutyl-phthalate, and di-2-ethylhexyl-phthalate. 

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