SU558639A3 - Method for preparing aminooxyhydroxamic acid derivatives or their salts - Google Patents

Description

(54) METHOD FOR OBTAINING DERIVATIVE AND-AMINOOXYHYDROXAMIC ACID OR THEIR SALT

one

This invention relates to a process for the preparation of novel a-amino-oxyhydroxamic acid derivatives or their salts of general formula I

X N - O - CH - C - NH - OY

R

ABOUT

where X is a methylene group substituted by nitrophenyl or nitrofuran residues,

R is hydrogen,

Y-alkyl group with 1-15 carbon atoms, halophenyl, or halobenzyl having biological activity.

The literature describes various a-aminooxyhydroxamic acids with free or acyl-substituted amino-oxy group 1, as well as Schiff bases of aminooxy-carboxylic acids 2, however, there is no mention of the method for preparing α-aminooxyhydroxamic acid derivatives of general formula I that have valuable properties.

The method according to the invention consists in that the α-aminooxyhydroxamic acid derivative or its salt of the general formula II

HsN-0 CH-C-NH-O-Y I II R O

where R and Y have the indicated meanings, are reacted with an oxo compound of general formula III

X 0

where X has the indicated values, preferably at O-40 ° C, in an organic solvent, preferably in dimethylformamide, or in a mixture with water, in the presence of an inorganic acid acceptor or tertiary amine.

The reaction mixture is left to stand at a commanding temperature of 30 minutes to 72 hours, preferably 1 to 16 hours. The solvent is removed and the target product is isolated in a known manner.

H p and me r 1. N- (N-furfurylideneamine oxyacetyl) -O- (n-dodecyl) -hydroxylamine.

1.20 g (0.0039 mol) of N- (amineooxyethyl) -0 (c-dodode yl) -hydroxylamine hydrochloride is dissolved in 10.0 ml of methylformamide. 0.58 cm (0.0039 mol) of triethylamine and 0.32 cm (0.004 mol) of furfural are added to the solution. The reaction mixture is left to stand at compati temperature for 16 hours and then the solvent is chased under reduced pressure. The residue is recrystallized from a mixture of ethanol and water in a 1: 1 ratio. Obtain 1.25 g (92% of theoretical) (FURFURiliden) -amiyooxyacetyl - 0- (k-dodecyl) -hydroxylamine, t. Pl. 58-60 ° C, R / 0.52. Calculated,%: C 64.8; H 9.0; N 8.0. CigHsjO Ns. Found,%: C 64.6; And 9.2; N 7.9. Example 2. (2,4-dinitrobenzal) aminooxyacetyl-0 - (4-chlorobenzyl) -hydroxylamine. From the corresponding starting materials, as in Example 1, (2,4-dinitrobenzal) -aminooxyacetyl-O- {4-chlorobenzyl) -hydroxylamine is obtained with a yield of 88% of the theoretical. The melting point of the product recrystallized from a mixture of ethanol and water was 104-106 ° C, R 0.22. Calculated,%: C 48.2; H 3.3; N 14.0. Ci6Hi307N4CL Found;%: 48.0; H 3.4; N 13.8. Example 3. N- N- (5-nitrofurfurylidene) aminooxyacetyl-0- (4-chlorobenzyl) -hydroxylamine. 1.56 g (0.005 mol) of M- (aminooxyacetyl) -0 (4-chlorobenzyl) hydroxylamine hydrochloride is dissolved in 7.0 cm of water, and 0.41 g (0.005 mol) of sodium acetate is added to the solution and then 0. 71 g (0.005 mol) of 5-nitrofurfural in 9.0 cm of methanol. The reaction mixture is stirred at room temperature for 2 hours. The mixture is then diluted with 13 cm of water. The product that has been precipitated is washed with water, dried and then recrystallized from ethyl acetate. Obtain 1.20 t (75% of theoretical) (5-nitrofurfurylidene) aminooxyacetyl) -O- (4-chlorobenzyl) -hydroxylamine, so pl. 110-111 ° C, R / 0.35. Calculated,%: C 47.5; H 3.4; N 1.9. SNN, 20bMzS1. Found,%: C 47.7; H 3.6; N 11.8. Formula - l a and 3 obre e and u Method of obtaining a-aminooxy-hydroxamic acid derivatives of general formula IX: iN-O-CH-C-NH-O-YR O where X is a methylene group substituted by nitrophenyl or nitrofuryl residues , R is hydrogen, Y is an alkyl group with 1-15 carbon atoms, halophenyl or halobenzyl, or their salts thereof, characterized in that the α-aminooxyhydroxamic acid derivative or its salt of general formula II HsN-O-CH-C-NH -O-Y where R and Y have the indicated meanings, are reacted with an oxo compound of the general formula III where X has the indicated Achen, in an organic solvent or a mixture of an organic solvent and water in the presence of an inorganic acid acceptor or a tertiary amine. Sources of information taken into account in the examination 1.Patent of Germany No. 2063996, class C 07C, A 61K, publ. 07.15.71. 2.E. Testa, B.J.R. Nicolaus, L. Mariani, J. Payani. Dber Synthese und Eigenschaften der a-Aminooxy-Carbonsauren, Analoga naturlicher a-Aminocarbonsauren. Helv. Chim. Acta, 1963, 46, c. 766.