3- Amino-4-toluic acid

The method is capable of extension to other o-amino-carboxylic acids,3 e.g., to 3-amino-2-naphthoic acid, 4,4 -di-aminobiphenyl-3,3 -dicarboxylic acid, and 2-amino-/>-toluic acid. With some acids other than anthranilic, difficulty may be encountered owing to the readiness with which their hydrochlorides are salted out of solution by hydrochloric acid. 

Terephthalaldehyde C(-Amino-/>-toluic acid p-Fluorostyrene- carbon monoxide Styrene-al carbon monoxide d-Hydroxystyrene-a/f-carbon monoxide Vinyl benzoate Phenylalanine Tyrosine... 

A variety of cleavage conditions have been reported for the release of amines from a solid support. Triazene linker 52 prepared from Merrifield resin in three steps was used for the solid-phase synthesis of aliphatic amines (Scheme 22) [61]. The triazenes were stable to basic conditions and the amino products were released in high yields upon treatment with mild acids. Alternatively, base labile linker 53 synthesized from a-bromo-p-toluic acid in two steps was used to anchor amino functions (Scheme 23) [62]. Cleavage was accomplished by oxidation of the thioether to the sulfone with m-chloroperbenzoic acid followed by 13-elimination with a 10% solution of NH4OH in 2,2,2-trifluoroethanol. A linker based on l-(4,4 -dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde) primary amine protecting group was developed for attaching amino functions (Scheme 24) [65]. Linker 54 was stable to both acidic and basic conditions and the final products were cleaved from the resin by treatment with hydrazine or transamination with ra-propylamine. 

The retention and the peak asymmetry of benzoic acid also indicate the inertness of the bonded phase. If basic compounds remain on the surface or are used as reagents, the peak asymmetry of benzoic acid is poor. The peak height is lower than that of the same quantity of o-toluic acid.3,4 This phenomenon is observed if the basic catalyst that was used in the synthesis process has not been completely washed off the stationary phase or if active amino groups remain. This type of column is not suitable for the separation of acidic compounds. 

For the synthesis of isoindoles (benzo[c]pyrroles) by type la cyclization the required intermediate is an o -acylbenzylamine. The only viable route to these substances which has been developed starts with a -bromo-o -toluic acid which is converted first to a phthalimide and then to the acid chloride. The acid chloride is then elaborated to the requisite ketone by Friedel-Crafts acylation. Condensation to the isoindole occurs on liberation of the primary amino group using hydrazine (equation 18) (64JA4152). 

Amino-benzyl alcohol m-Toluic acid m-Anisic acid... 

Toluenesulfonic acid, 24, 72 26, 19 -Toluenesulfonyl chloride, 20, 50 w-Toluenethiol, 27, 81 a-ToLUiC acid, ck-amino, dl, 22, 23 a-TOLUIC ACID, 0-CARBOXY, 22, 61... 

C8H8CIN03 4-amino-5-chloro 2-methoxybenzoic acid 7206-70-4 25.00 1.3446 2 13414 C8H802 p-toluic acid 99-94-5 126,85 1,2510 2... 

Closely related to these reactions with nucleophiles are those of aminotropones with nitrous acid. Thus from 2-amino-4-methyl-tropone and 2-amino-6-methyltropone no diazonium compound could be detected and the products were a mixture of m-toluic acid and either 2-hydroxy-6-methyl- or 2-hydroxy-4-methyl-benzaldehyde [206]. 

Amino-p-toluic Acid Homoait rnnUio ctctd). 

FIGURE 3.7 Comparison of theoretical and experimental adsorption isotherms of benzene derivatives. = Phenol A = Benzaldehyde = Benzonitrile = m. toluic acid, x = m.amino benzoic acid. (After Urano, K., Kochi, Y., and Yamamoto, Y, J. Colloid Interface Set, 86, 43, 1982. With permission.)... 

Anisic acid was used with benzoxazole, whereas /i-toluic acid was more suited for benzothiazole derivatives. Formamides bearing pyrrolidine, piperidine, and morpholine derivatives were viable coupling partners however, amido- and ester-substituted substrates were unreactive. Notably, an optically active formamide could function as a coupling partner without racemization, suggesting that optically active amino groups could be incorporated onto heterocyclic systems via this process (eq 19). 

---