CS208349B1 - Method of making the 6-n-acylamino-3-indazolones - Google Patents
Method of making the 6-n-acylamino-3-indazolones Download PDFInfo
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- CS208349B1 CS208349B1 CS205080A CS205080A CS208349B1 CS 208349 B1 CS208349 B1 CS 208349B1 CS 205080 A CS205080 A CS 205080A CS 205080 A CS205080 A CS 205080A CS 208349 B1 CS208349 B1 CS 208349B1
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- Czechoslovakia
- Prior art keywords
- indazolones
- acylamino
- amino
- indazolone
- acetic acid
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- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 239000012458 free base Substances 0.000 claims abstract description 5
- 238000002955 isolation Methods 0.000 claims abstract description 5
- -1 6-amino-3-indazolone dihydrochloride anhydride Chemical class 0.000 claims abstract description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 239000011734 sodium Substances 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- ADEYIUATTSJXLA-UHFFFAOYSA-N 6-aminoindazol-3-one dihydrochloride Chemical compound Cl.Cl.NC1=CC=C2C(N=NC2=C1)=O ADEYIUATTSJXLA-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- 235000011044 succinic acid Nutrition 0.000 abstract 2
- LGBOAAYNWOZWFE-UHFFFAOYSA-N 6-aminoindazol-3-one hydrochloride Chemical compound Cl.NC1=CC=C2C(N=NC2=C1)=O LGBOAAYNWOZWFE-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 150000003444 succinic acids Chemical group 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GBBHWGRJHHNAGT-UHFFFAOYSA-N 3-hexadecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC1CC(=O)OC1=O GBBHWGRJHHNAGT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006103 coloring component Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 1
- INEJTLPKMPELDM-UHFFFAOYSA-N 4-aminoindazol-3-one Chemical class NC1=CC=CC2=C1C(=O)N=N2 INEJTLPKMPELDM-UHFFFAOYSA-N 0.000 description 1
- ARDPDSOHNKVSMU-UHFFFAOYSA-N 6-aminoindazol-3-one Chemical compound NC1=CC=C2C(=O)N=NC2=C1 ARDPDSOHNKVSMU-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Způsob výroby 6-N-acylamino-3-indazolonů β volnou karboxylovou skupinou reakcí dihydrochloridu 6-amino-3-indazolonu s anhydridy kyseliny jantarové, který ee používá Jako barvotvorné komponenta pro purpurovou vrstvu barevného fotografického materiálu. 6-N-acylamino-3-indazolony obecného vzorce se podle vynálezu vyrábějí tak, že díhydrochlorid 6-amino-3-indazolonu se převede v prostředí kyseliny octové působením její eodné nebo draselné eoli na volnou bázi, která se bez izolace acyluje anhydridy kyselin jantarových, substituovaných alkylovou nebo alkenylovou skupinou s 12 až 18 atomy uhlíku při teplotě 60 až ilO °C.Process for preparing 6-N-acylamino-3-indazolones β free carboxyl group of reactions 6-amino-3-indazolone dihydrochloride anhydride succinic acid used by the ee As a colorforming component for magenta layer of color photographic material. 6-N-acylamino-3-indazolones the formulas according to the invention are produced such that: 6-amino-3-indazolone hydrochloride is converted in acetic acid by treatment its sodium or potassium free base, which is acylated with anhydrides without isolation succinic acids substituted with alkyl or an alkenyl group of 12 to 18 carbon atoms at 60 to 10 ° C.
Description
(54) Způsob výroby 6-N-acylamino-3-indazolonů(54) A process for the preparation of 6-N-acylamino-3-indazolones
Způsob výroby 6-N-acylamino-3-indazolonů β volnou karboxylovou skupinou reakcí dihydrochloridu 6-amino-3-indazolonu s anhydridy kyseliny jantarové, který ee používá Jako barvotvorné komponenta pro purpurovou vrstvu barevného fotografického materiálu. 6-N-acylamino-3-indazolony obecného vzorce se podle vynálezu vyrábějí tak, že díhydrochlorid 6-amino-3-indazolonu se převede v prostředí kyseliny octové působením její eodné nebo draselné eoli na volnou bázi, která se bez izolace acyluje anhydridy kyselin jantarových, substituovaných alkylovou nebo alkenylovou skupinou s 12 až 18 atomy uhlíku při teplotě 60 až ilO °C.A process for producing 6-N-acylamino-3-indazolones with a free carboxyl group by reacting 6-amino-3-indazolone dihydrochloride with succinic anhydrides, which is used as a coloring component for the purple layer of color photographic material. According to the invention, the 6-N-acylamino-3-indazolones are prepared by converting 6-amino-3-indazolone dihydrochloride in acetic acid by treatment with its sodium or potassium salt to the free base which is acylated without isolation with succinic anhydrides substituted with an alkyl or alkenyl group of 12 to 18 carbon atoms at a temperature of 60 to 10 ° C.
208 J49208 J49
208 349208 349
Předněten vynálezu Je způsob výroby 6-N-acylamino-3-indazolonů β volnou karboxylovou skupinou reakcí dihydrochloridu 6-amino-3-indazolonu 8 anhydridy kyseliny jantarové, obsahujícími alkylové nebo elkenylové skupiny s 12 až 18 atomy uhlíku.SUMMARY OF THE INVENTION It is a process for preparing 6-N-acylamino-3-indazolones with a free carboxyl group by reacting 6-amino-3-indazolone dihydrochloride with succinic anhydrides containing C 12 -C 18 alkyl or alkenyl groups.
N-acylaninoindazolony jaou barvotvornýhi komponentami pro purpurovou vrstvu barevného fotografického materiálu. K tomuto účelu se vyrábějí acylacl hydrochloridů amino-3-indazolonů zmíněnými anhydridy v pyridinu při teplotě varu uvedeného rozpouštědla, které současně věže uvolněný chlorovodík z výchozího hydrochloridu. V případě 6-aminoindazolonu vznikají za udaných podmínek barvotvorné složky obecného vzorce I kde R je alkyl nebo alkenyl e 12 až 18 atomy uhlíku, které neobsahuji volnou karboxylovou skupinu a pro jejich aplikaci do fotografické emulze je nezbytné štěpení imldového cyklu přebytkem alkalického hydroxidu, pokud se složky vpravuji do emulze ve formě alkalického roztoku. Při výrobě se komponenty izoluji z pyridinového roztoku po reakci srážením ve zředěné kyselině chlorovodíkové. Regenerace pyřidlnu z vod ného roztoku jeho hydrochloridu je obtížná a ekonomicky náročná. Nadto činí výtěžky komponent po čištění surových produktů zpravidla jen kolem 75 % teorie.N-acylaninoindazolones are color-forming components for the purple layer of color photographic material. For this purpose, acylacyl hydrochlorides of amino-3-indazolones are prepared by the said anhydrides in pyridine at the boiling point of said solvent, which at the same time tows the hydrogen chloride released from the starting hydrochloride. In the case of 6-aminoindazolone, the coloring constituents of formula (I) where R is alkyl or alkenyl containing from 12 to 18 carbon atoms which do not contain a free carboxyl group are formed under the specified conditions and are applied to the photographic emulsion. the ingredients are incorporated into the emulsion in the form of an alkaline solution. In production, the components are isolated from the pyridine solution after reaction by precipitation in dilute hydrochloric acid. Regeneration of fodder from an aqueous solution of its hydrochloride is difficult and economically difficult. Furthermore, the yields of the components after purification of the crude products are generally only about 75% of the theory.
Naproti tomu lze nevýhody odetrenit přípravou 6-N-acylamino-3-lndazolonů obecného vzorce II kde R je alkyl nebo alkenyl s 12 až 18 atomy uhlíku, vyznačený tím, že dihydrochlorld 6-amino-3-indezolonu se převede v prostředí kyseliny octová působením její sodné nebo draselné soli na volnou bázi, která ee bez izolace acyluje anhydridy kyselin jantarových, substituovaných alkylovou nebo alkenylovou skupinou e 12 ež 18 atomy uhlíku, pří teplotě 60 ež 110 °C. Oe výhodná provádět acyleci ve eměei kyseliny octové a nizkovroucích alifatických ketonů, e výhodou acetonu.On the other hand, the disadvantages can be eliminated by the preparation of 6-N-acylamino-3-indazolones of the general formula II wherein R is alkyl or alkenyl of 12 to 18 carbon atoms, characterized in that 6-amino-3-indezolone dihydrochloride is converted in acetic acid by its sodium or potassium salts on the free base which, without isolation, acylates succinic anhydrides substituted with an alkyl or alkenyl group of 12 to 18 carbon atoms at a temperature of 60 to 110 ° C. It is preferred to carry out acylcation in a mixture of acetic acid and low boiling aliphatic ketones, preferably acetone.
Příklad 1Example 1
V 250 ml ledové kyseliny octové ee pří 90 °C rozpustí 16,6 g bezvodého octanu sodného, k roztoku ee přidá najednou 22,2 g dihydrochloridu 6-amino-3-lndazolonu a po Smlnutovém promíchání 34,0 g anhydridu kyseliny hexadecyljantarová. Směs ee udržuje za mícháni při uvedená teplotě 0,5 h a pak ea ochladl na 15 až 20 °c. Hustě vyloučený produkt ee odfiltruje, promyje etenolem, vodou a vysuší při 80 °C. Získá ee 42,6 g (90 % teor.) komponenty vzorce II (R hexadecyl) e obsahem 99,8 % dle stanovení karboxylová ekupiny.16.6 g of anhydrous sodium acetate are dissolved in 250 ml of glacial acetic acid at 90 DEG C., 22.2 g of 6-amino-3-indazolone dihydrochloride are added in one portion and, after stirring, 34.0 g of hexadecylsuccinic anhydride are added. The mixture is kept under stirring at said temperature for 0.5 h and then cooled to 15-20 ° C. The densely precipitated product was filtered, washed with ethenol, water and dried at 80 ° C. 42.6 g (90% of theory) of the component of formula II (R hexadecyl) are obtained, having a content of 99.8% as determined by the carboxyl group.
208 349208 349
Přiklad 2Example 2
Ve 200 ml 90% vodné kyseliny octové se rozpustí 27,2 g krystalického octanu sodného, v roztoku se rozmíchá při 80 °C 22,2 g dihydrochloridu 6-amino~3-indazolonu a přidá sa 33,8 g anhydridu kyseliny hexadecyljantarové. Po 40 minutách míchání při 100 až 105 °C se směs zpracuje jako v přikladu 1. Ziská se 43,4 g (92 % teor.) komponenty vzorce II (R » hexadecenyl) s obsahem 99,6 % dle absorbance azometinového barviva s N,N-diatyl-p-fenylendiaminem.27.2 g of crystalline sodium acetate are dissolved in 200 ml of 90% aqueous acetic acid, mixed with 22.2 g of 6-amino-3-indazolone dihydrochloride at 80 DEG C. and 33.8 g of hexadecylsuccinic anhydride are added. After stirring at 100-105 ° C for 40 minutes, the mixture is worked up as in Example 1. 43.4 g (92% of theory) of the component of formula II (R ' hexadecenyl) are obtained with a content of 99.6% by absorbance of the azomethine dye with N , N-diatyl-p-phenylenediamine.
Přiklad 3Example 3
Do 190 ml ledové kyseliny octové se pomalým proudem vmíchá 30,3 ml 29% vodného roztoku hydroxidu draselného, přidá se 22,2 g dihydrochloridu 6-amino-3-indazolonu a roztok volné báze se zpracuje se 36,8 g anhydridu kyseliny oktadecenyljantarové jako v příkladu 2. Po digesci komponenty ve 200 ml etanolu se získá 40 g barvotvorné složky vzorce II (R = oktadecenyl).30.3 ml of a 29% aqueous potassium hydroxide solution are slowly stirred into 190 ml of glacial acetic acid, 22.2 g of 6-amino-3-indazolone dihydrochloride are added, and the free base solution is treated with 36.8 g of octadecenylsuccinic anhydride as in Example 2. After digesting the component in 200 ml of ethanol, 40 g of coloring component of formula II (R = octadecenyl) are obtained.
Přiklad 4Example 4
V 70 ml kyseliny octové se rozpustí při 60 °C 27,2 g krystalického octanu sodného a dále se postupuje jako v přikladu 2 s tim rozdílem, že anhydrid se přidává rozpuštěn ve 100 ml acetonu a acyluje se po dobu 1 h při mírném varu směsi. Při izolaci se komponenta promývá acetonem a vodou. Získá se 41 g (86 % teor.) produktu dle přikladu 2.27.2 g of crystalline sodium acetate are dissolved in 70 ml of acetic acid at 60 DEG C. and the procedure is as in Example 2 except that the anhydride is added dissolved in 100 ml of acetone and acylated for 1 hour with gentle boiling of the mixture. . For isolation, the component is washed with acetone and water. 41 g (86% of theory) of the product of Example 2 are obtained.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS205080A CS208349B1 (en) | 1980-03-25 | 1980-03-25 | Method of making the 6-n-acylamino-3-indazolones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS205080A CS208349B1 (en) | 1980-03-25 | 1980-03-25 | Method of making the 6-n-acylamino-3-indazolones |
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| Publication Number | Publication Date |
|---|---|
| CS208349B1 true CS208349B1 (en) | 1981-09-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS205080A CS208349B1 (en) | 1980-03-25 | 1980-03-25 | Method of making the 6-n-acylamino-3-indazolones |
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| Country | Link |
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| CS (1) | CS208349B1 (en) |
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1980
- 1980-03-25 CS CS205080A patent/CS208349B1/en unknown
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