Patent GB-642412-A (GB)
Title: Process of purifying aromatic 1-hydroxy-2-acid amides by conversion into aromatic oxazine diones and reconversion of the said diones to purified amides
IPC: C07D213/18
Filed: 1947-07-03
Abstract: A hydroxyarylcarboxylic acid amide of the formula RCONHA, wherein R is a hydroxyaryl radical and A an aliphatic radical containing at least 5 carbon atoms, an aromatic radical, or a heterocyclic radical, is purified by conversion to an oxazine dione and hydrolysis in an alkaline solution to the amide.  The amide may be converted to the oxazine dione by heating with an alkyl chlorocarbonate in a solvent-diluent which is or which contains an acid acceptor. Alternatively, an oxazine dione can be prepared by reacting an aromatic 1-hydroxy-2-carboxylic acid with an alkyl chlorocarbonate in a solvent-diluent to obtain an aromatic 1-carboalkoxy-2-carboxylic acid, converting to the acid chloride with thionyl chloride, reacting with an aliphatic amine containing at least 5 carbon atoms or with an aromatic or heterocyclic amine, and refluxing.  Alternatively, the amine may be reacted with an aromatic 1-hydroxy-2-carboxylic acid chloride in presence of a solvent diluent and the product refluxed with an alkyl chlorocarbonate.  Amides specified are 1-hydroxy - N - octadecyl - 2 - naphthamide - 4 - sulphonic acid, 1 - hydroxynaphthoylaminododecylaniline, 1 - hydroxy - 2 - naphthalenesulphonamido - 41 - octadecyloxybenzene - 4 - sulphonic acid, 1-hydroxy-2-naphthoylamino-41-methyloctadecylaminobenzene - 31 - sulphonic acid, 1 : 2 : 3 : 4 - xylenocarboylamino - 41 - perhydrodiphenylaminobenzene-31-carboxylic acid, and 1-hydroxy-2-naphthoylamino-21-methyloctadecylaminobenzene - 5 - sulphonic acid.  Aromatic 1-hydroxy-2-carboxylic acids specified are salicylic, 1-hydroxynaphthoic, 1-hydroxynaphthalene-2-sulphonic, 1-hydroxynaphthalene-6-sulphonic, 1 : 2 : 3 : 4-xylenolcarboxylic, 1-hydroxy-2-carbazolecarboxylic, 5 : 6-dimethoxyphenol - 2 - carboxylic, hydroxycinnamic, 2 : 6-phenoldicarboxylic, 1-hydroxy-6-methoxynaphthalene - 2 - carboxylic, and 5 - hydroxyquinoline-7-carboxylic acids. Amines specified are amylamine, isoamylamine, and hexylto octadecyl-amines, pentenylamine, isopentenylamine, and hexenylto octadecenyl-amines, cyclopentanylamine, cyclohexylamine, cycloheptylamine, and cyclo-octylamine, aniline, benzylamine, a  - naphthylamine, naphthmethylamine, ar.- and ac.-tetrahydro-1-naphthylamines, toluidine, xylidine, 1-amino-2-phenylethane, 1 - amino - 4 - methyloctadecylaminobenzene - 3 - sulphonic and -carboxylic acids, 1-amino-4-dodecylaminobenzene-3-sulphonic and carboxylic acids, 1 - amino - 4 - abietinylaminobenzene - 3 - sulphonic acid, 1 - amino - 4 - perhydrodiphenylaminobenzene - 3 - carboxylic acid, 1-amino-2-oleylaminobenzene-5-sulphonic acid, 1-amino-2-abietinylaminobenzene - 5 - carboxylic acid, p - stearylaminoaniline, o - methyldodecylaminoaniline, p - dodecylaminotoluidine, 4 - methyloctadecylamino-naphthylamine, o- and p-octadecylaniline, p - octadecyloxyaniline, p - stearoylaminoaniline, p - decylcarbamylaniline, p - dodecylaminoaniline, 4-methyloctadecylamino-1-aminocarbazole, 4-methyloctadecylamino-1-amino - 2 - ethoxybenzene, p - stearylamino - 1 - methoxyaniline, a - and b -aminofuran, furfurylamine, 3 - amino - 5 - pyrazolone, 1 - phenyl - 3 - amino - 5 - pyrazolone, 1 - (21 - benzthiazolyl) - 3 - amino - 5 - pyrazolone, 6-aminobenzthiazole, 6 - aminobenzoxazole, 2- and 3-aminoindole, and a - and b -aminopyrrole. In examples, compounds are prepared by reacting together: (1) 3 - amino-5-stearoylamino - p - toluenesulphonic acid and 1-carbethoxyoxy-2-naphthoyl chloride in pyridine; (2) as (1) followed by precipitation with alcoholic KOH; (3) 3-amino-5-stearoylamino - p - toluenesulphonic acid and 4-chloro-1-hydroxy-2-naphthoylchloride, and then with ethyl chloroformate; (4) 3-amino-5-stearoylamino-p-toluenesulphonic acid and 4-bromo-1-hydroxy-2-naphthoyl chloride, and then with ethyl chloroformate; (5) 1-hydroxy-N-octadecyl-2-naphthamide-4-sulphonic acid (pyridine salt) and ethyl chloroformate; (6) 3-amino-5-stearoylamino-p-toluenesulphonic acid and 2-carbethoxyoxy-3-cresotinoyl chloride; (7) 4-chloro-1-hydroxy-2-naphthoyl chloride, and sodium 3-amino-4-methyloctadecylaminobenzenesulphonate, and then with ethyl chloroformate; and (8) furfurylamine and 2-carbethoxyoxy-3-cresotinoyl chloride.