SU468418A3 - The method of obtaining 1-hydroxy-2-pyridone - Google Patents

Description

 1 The invention relates to an improved, production method. Boxy-2-pyridone ,. known for its high antibacterial and antifungal activity. A known method for the preparation of 1-hydroxy-2-pyridones is the reaction of 2-pyrons with hydroxylamine in the presence of pyridine. However, the yields of the target products are very low and. Obtaining the target 1-hydroxy-2-pyridones in this way is practically impossible. According to the proposed method, 2-pyrones can be converted into 1-, hydroxy-2-pyridones of high purity by a universal method with xopo-yields by reaction with hydroxy: lamine. or its salts in moderate. conditions in the presence of aminopyridines or imidazoles. Thus, from 4-methyl-6-cyclohexyl-2-pyrone, by heating for 8 hours with hydroxylamine hydrochloride in pyridine, the corresponding 1-hydroxy pyridone is obtained in a yield of 2.6% of theoretical. If, instead of pyridium, a-picoline is used, the yield is 3.0%. However, if, all other things being equal, pyridine is replaced with the proposed amines, then the yields of the desired reaction product increase by about 20 times. For example, when using 2-amino-1-chridine, it is 49%, when using 2-amino-6-methylshridika — 47%, when using 2-amino-4-methyl-pyridine — 53%, when using imidazole — 47% of the theoretical, i In addition, the product obtained by the proposed method is characterized by a high degree of purity. According to the proposed method, it is possible to obtain 1-hydroxy -2-pi yloxy 1 general form L1 L O in which RI y) is an alkyl radical branched, if necessary, with 1-17 atoms carbon, Eugenyl radical with 2-17 carbon atoms, cycloal; keel radical with 3-8 carbon atoms, cyclopyl alkyl radical, phenyl, fash1l yn :),. alkylalkyl, beizhydryl,; ieHpKQMM THJibHbrii, phenylmer | aptomethyl; fesul1fometil1nh), 1i h. substituted in aromaticsbd; /: 0dn | y1 non-alkyl, alkoxy xy1 1NO-, nitro; alg i coxcapbonyl-; cyano groups or atoms: halogen radicals, furyl or furylalkenyl radicals; 2 is hydrogen, H1 | ish alkyl, alkenyl, alkynyl or benzyl radicals, and 2 together with / Zj or from may form a 5- or 6-membered ring; i 3 hydrogen, lower alkyl or phenyl radical; 4 - hydrogen, lower alkyl, alkenyl, methoxymethyl or benzyl radicals or a halogen atom, by the interaction of a 2-pyrone of the general formula in which I, - Rj, have a terminal value; - .. with hydroxylamine or its salts in the presence of amines, which use substituted or unsubstituted aminopyridines or imidazoles. i Among these —R alkyl radicals, preferred is VL. lower alkyl radicals with 1-4 carbon atoms, in particular one and two carbon atoms, among alkenyl radicals - radicals with 2-4 carbon atoms. Among the radicals containing the phenyl colo, preferred are unsubstituted phenyls or substituted with one or two substituents, and among the phenylalkyl radicals, the benzi-ndai radical. The reaction can be carried out within a wide temperature range, for example: between room temperature and or even higher. In most cases, satisfactory reaction rates are 50 to 50 ° C. Perhaps, however, in the general case, it is not required, the addition of solvents which are inert at these conditions, or dilutions of the Filters. In special cases, the addition may seem preferable. Such solvents or diluents may be polar or incomplete, miscible or immiscible with water, i For example, the following compounds can be used: water, lower alcohol {for example, methyl, ethyl,; isopropyl alcohols), ethylene glycol, ethylene glycr-monomethyl ether; propilentlikol, amines (e.g., triethylamine, morfoliNr pyrrolidine, piperidine, pyridine, picoline), acid amides (e.g., formamide, dimethylformamide, diethyl | lformamid, monometilatsetamil, UU-methyl-pyrrolidine, hexamethylphosphoric triamide), slozhile esters (e.g., ethyl acetate , methyl propionate, ethylene carbonate), ethers (e.g., diethyl, diisopropyl ether, dioxane, tetrahydrofuran), hydrocarbons (e.g., methylene chloride, chlorobenzene), nitro compounds (e.g., nitromethane, 2-nitropropane, Nitrobenzene), nitriles (nitromethane, nitrile) (e.g. cetonitrile, propionitrile, benzonitrile), and also demethylsulfoxide, tetramethylene sulfone, etc. The amines should be mentioned amy nipyridines and imidazoles, including those substituted in the ring or on the amino group with i and alkyl radicals, including 2 aminopyridine, Z-aminopyridine, 4-aminopyridine, 2-methylaminopyridine, 2-ethylaminopyridine, 2-amino-4-methyl-pyridine, 2-amino-6-methyl-pyridine, 2-amino-4 - ethyl pyridine, 2 -aminOg, b-Dimethyl-pyridine, 3-amino-6-methyl-pyridine, imidazole, methyl-imidazole, 2-methyl-imidazole, 4-methyl-imidazole, 2-ethyl.imidazole, narc do with the compounds from which they are produced. YaredI is respectful of methyl derivatives of both heterocycles, due to their easy technical availability, low molecular weight and high dissolving capacity for the components involved, not only for organic components, but also for hydroxylamine salts. -Because most of these compounds

five

are solid at room temperature, it may be preferable to change the liquid mixtures of these compounds if they want to react at low temperatures, for example at. i I The amine used is preferably used in an equimolar amount in the calculation of:; those per hydroxylamine salt. True, part 1, it can be replaced with other organic acid acceptors; or inorganic, but this will result in; a noticeable increase prrdrlzhite; to react; However, it can also complicate Ryo, the generation of an amine, which by distillation or extraction is easily accomplished as a result of the introduction of such additives. On the other hand, the use of a large excess of aminosilane or imidazole, for example, 20-fold molar kolichesta; the hydroxylamine salt does not have any negative influence on the course I of the reaction,

I Hydroxylamine or its salts can be used in equimolar amounts based on the 2-pyrone being reacted, 1 however, in order to speed up the reaction and increase the yields, it can be used in excess, for example in an amount of 5 or 10 moles per 1 mole 2-pyrone ,. It may also be advisable to add hydroxylamine in several portions during the reaction. : The resulting compounds are, for example, the following: i 1-hydroxy-6-methyl-2-pyridone; 1-hydroxy-4,6-dimethyl-2-pyridone;

1-OXY-: 3,4,6-trimethyl-.2-pyridone; 1-OXY-4,5,6-trimethyl-2-pyridone 5 1-hydroxy-4t Methyl-6-Ztil-2; pyridone; 1, hydroxy-4-methyl-6-isoprosyl-L-2-pyridone; 1-hydroxy-4-methyl-6-heptyl-2-pyridone; 1-hydroxy-3,4, -dimethyl-6-b-octyl-2-pyridone; 1-hydroxy-4-methyl-6-undecyl-2-1 garedone; , 1-.oxy-3,4-damethyl-6-heptadecyl-2-pyridots; 1. Oxy-4-ethyl-b, 6-Dimethyl-2-pyridone; 1-OXY-4,5-trimethylene-6-methyl-2-pyridone; 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone; 1-hydroxy-4-methyl-8-cyclohexmethyl-2-pyridone; : L-oxy-4-methyl-6-cyclohexylethyl-2-pyridone; Looxy-4-methyl-6-isobutec-L-2-pyridone; Oxy-4,6-dimethyl-5-benzyl-2-pyridone; 1-.oxy-3-benzyl-4,6-dimethyl-2-Sh1-idone; 1-oxy-4-methyl-b-benzyl-2-pyridone;

;; S,

1-hydroxy-4-methyl-6- (44chlorobenzyl) -2-pyridone;

1-hydroxy-b-phenylsulfonylmethyl-2-pyridone;

1-.OXY-3,4-Dimethyl-6- (4 chlorophenylsulfonylmethyl) -2-pyridone 5 5 L 1-hydroxy-3-bromo-4,6-Dimethyl-2-pyridone;

1-hydroxy-3-chloro-4-methid. In- (4-bromobenzyl) -2-pyridone;

 1 -oxy-3,4-diamethyl-6- (2,4-dimethylbenzyl) -2-pi10; ridon;

L-oxy-4-methyl-b-benzhydryl-2-S1-eridon; Hydroxy4-methyl-6- (4g Chlorophenoxymethyl) -2-sh1_rido 1 1-c1xi-4 - Mbe and -b7 (, p-trI5 {lrrphenoxymethyl) 3-2-pyridone ;; ;: - 15G 1-.oxy-4-methyl-b- (3 nitrp41enoxymethyl) -2-Sh1riflOHj.;

1-hydroxy-4 methyl-in- (phenylmercaptomethyl) -2-pyridone;

1-; hydroxy-4-methyl-6-phenyl-2-pyridone;

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1-.oxy-4-.methyl-6- (4-Tolyl) -2-Sh1ridone;

1. Oxy-3,4-Dimethyl. In - {4-tolyl) -2-pyridone;

1-bxi-4-methyl-8- (2,4-xylyl) -2-pyridone ;;

1. Oxy-4-methyl-6- (4- | Chlorophenyl) -2-pyridone;

1 hydroxy-3,5,6-trimethyl-4-ethyl-2-pyridone;

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1-hydroxy-4-methyl-5-ztil-6- (4-tolyl) -2-pyridone;

1-.oxy-4,6-diphenyl-2-pyridone;

1 bxy-4-fesh1l-6-methyl-2-pyridone;

1-; hydroxy-3-dtil-4 methyl-6- (4-.tolyl) -2-pyridone; :

thirty

1, hydroxy-4-methyl-6- (4-Sh1Trophenyl) -2-pyridone; :

1: hydroxy-4-methyl-6- (4-methoxyphenyl-2-shiridone;

1. Oxy-4-methyl-6-phenyl-5,2- (2-methylethylene) -2-pyridone; .

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1; hydroxy-4 methyl-b- (4 hCianfenoxymethyl) -2-pyridone; : /, ;;.,,. ;. .

1-.oxy-4-mvtil - & - (2-methoxycarbonylphenylmethyl) -2-pyridone; : - ..:,.

1-; hydroxy-4-methyl-6-furyl-2-pyridone;

40,

1-hydroxy-4-methyl-6- (2-furyl-vinyl) -2-pyridone;

1-hydroxy-4-methyl-6-styryl-2-pyridone;

1-Oxy-41methyl-in- (4-dimethylaminostyryl) -2-pyridone;

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1. Oxy-4-methyl-6- (4-1-phenyl-butadienyl) -2-pyridone;

14oxy-3-methoxymethyl-4 methyl-6- (4-tolyl) -2-pyridone;

1-hydroxy-3-allyl-4-methyl-6-phenyl-2-pyridone;

50

1. Oxy-4-methyl-5-allyl-in-phenyl-2-pyridone;

1-, hydroxy-4-.methyl-5-propargyl-6-phenyl-2-11 iridone;

Example 1.2g 4-methyl-6-Cyclohexyl-2-pyrone is heated with 1 g of hydrochloride hydroxide

S5 silamine and 5 g of 2-aminopyridine flow 8 hours to 80 ° C. Then the reaction mixture

.: 7. extracted with methylene chloride, the amine is removed by shaking with dilute hydrochloric acid from the organic phase, the reaction product is extracted with dilute sodium hydroxide solution and the basic solution is acidified with acetic acid to pH 6. 11. Oxy-4 methyl-6-cyclohexyl-2-pyridone precipitates as crystals, which are filtered, washed with water and dried. The product yield is 1.05 g (49% of 1 Theoretical), m.p. 143C (calculated by L (8.8%. Found, 8%). With firm equal conditions of reaction, using and 2-amino-4 methylpyridine get 1.15 g (yield 53% of theoretical), using 2-amino- 6; letyl-pyridine - 1, B1: g (47% of the theoretical), with the use of 3-aminopyridine - 0.52 g (24% of the theoretical), with the use of imidazole-1,01 (47% of the theoretical), while using pyridine, only 0.056 g (yield; 2.6% of the theoretical) is obtained, while using a-picoline — 0.0565 (3.0% of the theoretical) 1-hydroxy-4 cyclohexyl-2- {shrydon. Example 2 2 g W-benzyl. 4,6-dimeti -2-pyrone, 6 g of 2-aminopyridine and 1 g of hydroxylamine hydrochloride are scorched for 8 hours; BEFORE. After the decommissioned decommissioned at measure 1, 0.65 g (30% of theoretical joroKoro) 1-oxy-3- benzyl-4,6-Dimethyl-2-pyridone | st, mp, 14800 (calculated by VU 6.1; found / V6.1%:; If, all other conditions being equal, i use pyridine instead of aminopyridane, then 1-hydroxy | 2-pyridone is not formed at all, 1 P p and me p 3. i2 g of 4-methyl-6-benzyl-2-pyrone,: 6 g of 2-aminopyridine And 1 g of hypochloride hydro | silimin is heated for 5 hours before I 1.41 g of 1 (66% of theoretical) 1-ox -4-Methyl-6-h ben1zil-2-pyridone with m, mp. (calculated / V; 6.5%; found / V 6.8%) If, with other things being equal, aminopyridine is replaced by imidazole, then the EXIT is 1.33 g (62% of the theoretical), while using pyridine — only 0.26 g I (12% of theoretical). The products obtained using aminopyridine and imidazole are pure white, while using pyridine, a preparation is obtained which changes color to yellowish,

8 Example 4. 2 g of 4,6-dimethyl-5-benzyl-2-pyrone, -4 g of 2-aminopyridine and 0.9 g of hydrochloride: and hydroxylamine are heated for 5 hours before. I After the usual separation, 0.89 g (42% of the theoretical) are obtained 1.; s (xi-4,6-dimethyl-5-benzyl-2-pyridone with mp, 165 ° С (you have N 6, 1%, found L 6,1%).: Under comparable conditions, it is obtained from 4-methyl-6-phenylsulfonylmethyl-2-pyrone-1. Hydroxy-4-methyl-6-phenylsulfonylmethyl-2-pyridone with m. ABOUT (yield 36%. Calculated / V 5.0%; found YY 5.1%); from 4-ethyl-5,6-dimethyl-2-pyrone-1.oxy-4-ethyl 5,6-dimethyl-2g pyridone with mp 1390C (yield 33%. I Calculated L 8.4%; found 8.2%); from H-bromo-4,6-Dimethyl-2-pyrone-1-hydroxy-3-bromo 4, 6 -Dimethyl-2-pyridone with m. PL, (yield 37%, calculated / V 6,4%; found / V 6,3%); from 4-methyl-6-isobut nyl-2-pyrone-1-hydroxy-4-mvtil-6-isobutenyl-2-pyridone — t, mp, (Yield 24%. Calculated / V 7.8%; found L 7.7%); out of 3 , 4-dimethyl-6- (4-Tolyl) pyrone-1-hydroxy-3,4 dimethyl-6- (4-Tolyl) -2-pyridone with m, pl, 125 (Yield 41%, Calculated / V 6, 1%; found L (5.8%); from 4-methyl-5-ethyl-6- (4-tolyl) -2-pyrone. 1-hydroxy-4-methyl-5-ethyl-6- (4-tolyl ) -2-pyridone f t pl, 1VOOS (Yield 49%. Calculated N 5.8%; found yV5.8%); from 4-methyl-6- (4 chlorophenoxymethyl) -2-pyrone-1-hydroxy-4-methyl-6- (4-.chlorophenoxymethyl) -2-pyridone with m, pl. 1610С (Yield 37%. Calculated L / 5.3%; found N 5.6%); from 4-methyl-6-phenylmercaptomethyl-2-pyrone-. -1-hydroxy-4-methyl-6-phenylmercaptomethyl-2-1 iridone with m, pl, 126 ° C (Yield 43%. Calculated N 5.7%; found L / 5.8%); from 4,6-dimethyl-2-pyrone-1-hydroxy-4,6-dimethyl-2-pyridone with m, pl, 135 ° C (Yield 46%. Calculated but L 10.0%; found to be L 10 ,one%); from 3.4, & -trimethyl-2-pyrone-1-hydroxy-3,4,6-trimethyl-2-pyridone with t, pl. 130 ° С (Yield 41%, Calculated N9.2%; found / V 9.4%); from 6-methyl-2-pyrone -} - hydroxy-6-methyl-2-pyridone with m. pl. 1141 OS (34% yield, Calculated N11.2%; A / 11.0% found); from 4-methyl-6-heptyl-2-pyrone-1-bxy-4-methyl-6-heptyl-2-pyridone with t, mp, (Yield 38%. Calculated N 6.3%; found L 6.0 %); from 4-methyl-6-undecyl-2-pyrone-1.oxy-4-methyl-6-undecyl-2-pyridane with mp, (Yield 33%. Calculated And 5.0%; found L5.4% ); from 4,5-trimethylene-6-methyl-2-pyrone-1.axi-. -4,5-trimethylene-in-methyl-2-pyridone with so pl. i (Yield 44%. Calculated N 8.5%; found V 8.4%) ;; from 4-methyl-6- (4-chlorophenyl) -2-pyrone-1-.oxy-41-methyl-6- (4-chlorophenyl). tfidone with m.p. 123C (Yield 26%. Calculated V 6.0.%; Found N 6.1%): .- - of 4, b-diphenyl-2-gopan-1.-oxy-4,6-Difeshl-2-pyridone with t pl. (Yield 91%. Calculated L 5.3%; found L 5.3%); from 4-methyl-6- (b; -furyl) -2-pyrone-1 hydroxy-4-gMe. Tyl-6- (a-furyl) -2-11 iridone with m. pl. (Yield 26%. It was calculated L 7, E%; found N 7.6% from 4-methyl-6- 2- (a. Furyl) -vinyl -2-pyrone-1oxy-4-methyl-6- 2- ( 1-furyl) -vinyl -2-pyridone with mp 166 ° C (Yield 28%. Calculated N 6.5%; found L6.4%); from 4-phenyl-6-methyl-2-11 -iron- Loxy-4 phenyl-6methyl-2-1 Shridon with mp. Il85C (Yield 62%. Calculated / V 7.0%; found Y 6.7%); from 4-methyl-6-otsch) and Lg2-pyroc .1.oxy-4-metile-6-styryl-2-pyridone. 0: t front 17600 (Yield 34%. Calculated L 6.2%; found N 6.0%); from 4-methyl-6- 4-phenyl-butadiene (1) -yl -2-pyro. on -1-oxy-4 methyl. 6-C4-phenyl-butadiene (1) -yl}. - pyridone with m. pl. (Yield 49%. Calculated / V 5.5%; found V 5.5%); , from 4-methyl-6- (4 yitrophenyl) -2-Pyrosh-1-hydroxy-4-methyl-6- (4-nitrophenyl) -2-Shfidon with mp, (Yield 18%. Calculated / V 11.4%; find., But M0.9%). . Example 5. 1g of 4-methyl-6- (4-tolyl) -2-Shfo; on, 0.6 g of hydroxylamine hydrochloride and 4 g of 2-g 1 -minopyridine are heated for up to. After the usual separation, 0.173 g (16.1% of theoretical) of 1-dKCH-4-We with 6-tyl (6-tolyl) -2-pyridone with m.p. (calculated / V 6.5%; found L 6.6%). If, other things being equal, pyridine is used instead of aminopyridine, the yield is only 0.012 g (1.1% of the theoretical). Under the same conditions, 1-hydroxy-4-methyl-b-fvnil-2-pyridone with m.p. 135 ° C (calculated / V 7.0%; found / V7.0%), and when using 2-aminopyridine, the yield is 17.2% whereas when using pyridine, only Pr and me 6. 1 g 4-methyl-6- (4-dimethylamino. Styryl) -2-pyrone, 3 g of 2-aminopyridine and 0.4 g of hydroxylamine hydrochloride are heated for 10 hours before. (The reaction product is precipitated by the addition of water. T. pl. I about, yield 0.91G, 86% of the theoretical (calculated N 10.4% ;; found L 10.0%). I; , Proceed analogously to Example 4, but 2-amino-b-methyl-pyridine was used instead of 2-aminopyridine to obtain 1. Oxy 4-methyl-6-cyclohexylmethyl-2-pyridone with mp 131 (Yield 44% Calculated (V 6,3%; find JH; v 6,5%); .. from 4 methyl-6-isopropyl-2-pyrone-1.-oxy-4-me; tyl-6-isoprosyl-2-pyridone with mp. (You; stroke 47%. Calculated by L 8.4%; found / V 8.2%); I of 4-methyl. 6- (4-methoxyphenyl) -2-Pyrone-G-hydroxy. | -4-methyl-b- (4-methoxyphenyl) -2-pyridone with mp i 174 ° C - (Output 23%. Calculated N 6.1%;: found W / 5.9%); .-.::..:., :: ::. From 4-mvtil-b-phenyl, 5.2- (2 -methylethylene) -2-pi-ppha1-1-bxI4-methyl-6-phenyl-5, 2- (2-methylethylene). -2-pyridy 1.e t, mp 174 ° C (Yield 26%. Calculated by W 5 , 8%; - found L (5.6%); from 4-methyl-6- (3-nitrophenoxymethyl) -2-pyrone. -1-hydroxy-4-.methyl-6- (3-nitrophenoxymethyl) -2- Pyridon with m. Pl. 216 (Yield 34%. Calculated / V 10.2%; found V 10.0%); : from 4 hMethyl-6-Ztil-2-pyrone-1.oxy-4-methyl-6-ethyl-2-pyridone with m. pl. (Yield 41%. Calculated L9.2%; found L9.4%); from 3-yl-4-methyl-6- (4-tolyl) -2-pyrone-1-hydroxy-3-zl-4-t-Methyl-6- (4pTolyl) -2-pyridone with m. pl. (Yield 29%. Calculated / V 5.8%; find. De Af 5.5%); ... from 3-methoxymethyl-4gK etil-6- (4-Golyl) -2-Pirona-l40xy-3-Me to T-methyl-4-Methyl-6- (4-tlil) -2pyridone with m. pl. (Yield 51%. Calculated V 5.4%; found W 5.4%); from 4 Methyl-6- (B-cyclohexylethyl) -2-pyrone. hydroxy-4-methyl-6-& -1 iclohexylethyl) -2-pyridone with so pl. (Yield 41%. Calculated N 6.0%; found N 5.8%); from 4-methyl-6-benzhydryl-2-pyrone-1-s (xi-4-methyl. in benzhydryl-2-pyridone with mp 191 C (Yield 33%. I Calculated / V 4.7%; Found L / 4.7%) j Example 8. 1g of 4-methyl-5-propargyl-6-phenyl-2-pyrone, 1.5 g of hydrochloride with hydroxyl per and 3 g of 2-amino-4-methyl-pyridine are heated for 9 an hour before. After the usual separation, 0.82 g (77% of a theoretical 1) is obtained. 1. Oxy-4-methyl. 5-1fopargil-6-pheny l-2-11 iridone with mp (calculated N 5.9% ; naydeno N 5.8%.) Under the same conditions, the following is obtained: from 3-allyl-4 1etyl.6. phenyl-2-11iron-1.} xi-3. allyl.4-methyl-b-phenyl -2-Yiridon with mp. Il5 ° C (Yield 60%. I Calculated N 5.8%, found N 5.7%); C 4-1Aethyl-3-allyl-6-phenyl-2-111.1. 1 bxy-4methyl-5-aldal-6-phenyl-2-pyridone with mp 176 ° C (yield 56%. Calculated: L 5 , 9%; found N 5.5%.) Example 9. i5r 4-1Lethyl-6- (F. chlorobenzyl). -2-yrone, 2.5 g of hydroxylamine hydrochloride and 10 g of 2-aminopyridine are heated for 16 to 60 ° C. After the usual separation: 3.3 g (62% of theoretical) are obtained: 1; 0xy. -4-Aethyl-6- (4-Chlorbeyuyl). 2-11 iridone with m.p. : 142 ° С (calculated by UU 5.6%; found L 5.9%). I try on. South 4-1Letil-6- (2.44-1-rimethylpentyl) -2-11-yrone, 5 g of hydroxylamine hydrochloride and 20 g of 2-yminopyridine are heated to: 26 hours to 70 ° C, and after | 17 hours, the following 2 g of hydroxyl I per reaction mixture are separated and 17.1 g (67% of theoretical) are obtained 1. (xi-4-.1-methyl, 1-6- (2,4,4 -1-methylmethyl) -2-11 iridone with t 180 ° C (calculated N 5.9%; found N 5.9% :). I Example Il.i2r 4-4methyl-6-1 iclohexyl-21-pyrone and 1 g of hydroxylamine dissolved in; shesi from 1.5 g of 2-Sh 1inosh1ridina and 4.5 g of 2-a1mij no-6-methylpyridine and incubated for t9 days at room temperature, After i ordinary rashes get 0.79 g (37% of theoretical I) 1-ox1; 47met1 lg1b.cyclohexyl) -2-pyridone with m. pl. . i V.-.-: .., Example 12. 1 g of 3,4-. Dimethyl-6- (2,4-Dimethyl; benzyl) -2-11irone, 0.5 hydroxylamine hydrochloride and 3 g of imidazole are heated for 18 hours before and then the reaction mixture is divided in the usual way. I Get 0,63 t (59% of theoretical) 1-C1XY-3,4-dimethyl-6- (2,4-Dimethyl-benzyl) -2-pyridone with so pl. (calculated / V 5.4%; found L5.6%.) If, other things being equal, pyridine is used instead of imazd azole, the yield is 0.003 g (0.3% of the theoretical). Example 13. 20 g of 41-methyl-6-Cyclohexyl-2i-pyrone, 8 g of hydroxylamine sulfate and 50 g of imidazole are heated to. ; For the next 3 hours, add the next 10 g of hydroxyl amine sulfate in portions. After 5 hours, the reaction mixture is separated. 11.8 g are obtained; 1 dxy-41Letil-6-1 clohexyl-2-pyridone with t. Pl. l430C. I Example 14. 2 g of 4-1 1-methyl-6-cyclohexyl-2; -g1iron,; 1.3 G; hydroxylamine sulfate and 5 g | them:} ОДАГйгрева19ТЭ during das d. . :: - :. , .- :: f-:: Output l-, uKCii ef 3k ii} / i & fl available), hereinafter. If the reaction is carried out with 15 minutes of heating to 150 ° C, the output is 0.94 g. I Example 15. 1 g of 4-yl-6-Cyclohexyl-2-Peron, 0.5 g of hydroxylamine hydrochloride, 2 g of aminopyridine and 1 g of toluene are heated for 5 hours to. After about an hour, the original two-phase system. becomes homogeneous. The yield is 0.44 g. If, instead of toluene, 1 g of glycol monomethyl ether is added, the yield is 0.47 g. 1 Subject of the invention 1. Method of preparing 1.xii-2-11 iridones by volume. u formulas in which D | is an alkyl radical, branched chain, if necessary, with 1-17 carbon atoms, an alkenyl radical having 2-17 carbon atoms, a cycloalkyl the radical of 3-8 carbon atomaksh, tsiklogeksilalkilny radical, phenyl, phenylalkyl, fenilalkenilny, benzhydryl, phenoxymethyl, fenilmerkaptometilny , phenylsulfomethyl, substituted in the case of necessity in the aromatic nucleus of one silt “by several alkyl, alkoxy-, amino-, 1-gly, alkoxycarbonyl-, cyanic groups or halogen atoms, radicals, furyl or furyl kenilny glad Isa s;