SU333168A1 - METHOD OF OBTAINING SUBSTITUTED HYDRAZONES DERIVATIVES OF 4-CARBOXY-2-QUINOLILALDEHYDE - Google Patents
METHOD OF OBTAINING SUBSTITUTED HYDRAZONES DERIVATIVES OF 4-CARBOXY-2-QUINOLILALDEHYDEInfo
- Publication number
- SU333168A1 SU333168A1 SU1327013A SU1327013A SU333168A1 SU 333168 A1 SU333168 A1 SU 333168A1 SU 1327013 A SU1327013 A SU 1327013A SU 1327013 A SU1327013 A SU 1327013A SU 333168 A1 SU333168 A1 SU 333168A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxy
- quinolilaldehyde
- obtaining substituted
- substituted hydrazones
- derivatives
- Prior art date
Links
- 150000007857 hydrazones Chemical class 0.000 title description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- -1 4-carboxy-2-quinolyl aldehyde Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UIDHNPTVQFNWOJ-UHFFFAOYSA-N 2-methylquinoline-4-carboxylic acid Chemical class C1=CC=CC2=NC(C)=CC(C(O)=O)=C21 UIDHNPTVQFNWOJ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BEFFPQBJNOEBQF-UHFFFAOYSA-N 2-formylquinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC(C=O)=NC2=C1 BEFFPQBJNOEBQF-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к получению новых соединений, которые могут найти применение в качестве физиологически активных веществ.The invention relates to the preparation of new compounds that can be used as physiologically active substances.
Предлагаемый способ получени замещенных гидразонов производных 4-карбокси-2хинолилальдегида заключаетс во взаимодействии производных 4-карбокси-2-хинолилальдегида с замещенными гидазина в водном растворе или в среде органического растворител .The proposed method for the preparation of substituted hydrazones of 4-carboxy-2-quinolyl aldehyde derivatives consists in the interaction of 4-carboxy-2-quinolyl aldehyde derivatives with substituted hydazine in an aqueous solution or in an organic solvent medium.
Показано, что производные 4-карбокси-2хинолилальдегида могут быть получены с количественным выходом при окислении замещенных 2-метилхинолин-4-карбоновой кислоты двуокисью селена в среде диоксана и с последующей его отгонкой в вакууме.It was shown that 4-carboxy-2-quinol-aldehyde derivatives can be obtained in quantitative yield by oxidation of substituted 2-methylquinoline-4-carboxylic acid with selenium dioxide in dioxane and its subsequent distillation in vacuum.
Полученные продукты могут быть использованы дл дальнейших целей без дополнительной очистки.The resulting products can be used for further purposes without further purification.
Структура полученных веществ подтверждена данными элементарного анализа и методами спектроскопии.The structure of the obtained substances was confirmed by elementary analysis data and spectroscopy methods.
Пример 1. 4-карбокси-2-хинолилальдегид моногидрат.Example 1. 4-carboxy-2-quinolyl aldehyde monohydrate.
К смеси 1,87 г (0,01 моль) 2-метилхинолин4-карбоновой кислоты и 2,0 г (0,002 моль) двуокиси селена прибавл ют 20 мл диоксана, смесь энергично перемешивают, температуру поднимают в течение часа до 100-110°С и выдерживают при ;вышеуказанной температуре (при энергичном перемешивании) в течение 4 час. Реакционную смесь отфильтровывают от селена, фильтрат упаривают почти досуха в вакууме (температура вод ной бани 50-60°С). Остаток раствор ют в 60 мл спирта и кип т т с активированным углем в течение 15-20 мин, гор чий раствор отфильтровывают от угл , фильтрат охлаждают до комнатной температуры и выдерживают в течение 12 час на холоде. Получают 1,98 г (90,4% от теории) моногидрата 4-карбокси-2хинолилальдегида , т. пл. 217°С. Далее перекристаллизовывают из спирта, т. пл. 209- 210°С. Найдено, %: С 60,56; Н 4,01; N 5,98, 6,16.20 ml of dioxane are added to a mixture of 1.87 g (0.01 mol) of 2-methylquinoline4-carboxylic acid and 2.0 g (0.002 mol) of selenium dioxide, the mixture is vigorously stirred, the temperature is raised to 100-110 ° C in one hour and maintained at the above temperature (with vigorous stirring) for 4 hours. The reaction mixture is filtered from selenium, the filtrate is evaporated almost to dryness under vacuum (water bath temperature is 50-60 ° C). The residue is dissolved in 60 ml of alcohol and boiled with activated carbon for 15–20 minutes, the hot solution is filtered from carbon, the filtrate is cooled to room temperature and kept for 12 hours in the cold. 1.98 g (90.4% of theory) of 4-carboxy-2-quinolylaldehyde monohydrate are obtained, m.p. 217 ° C. Then recrystallized from alcohol, so pl. 209-210 ° C. Found,%: C 60,56; H 4.01; N 5.98, 6.16.
C,iH9NO4.C, iH9NO4.
Вычислено, %: С 60,27; Н 4,14; N 6,38.Calculated,%: C 60.27; H 4.14; N 6.38.
Аналогичным способом получают 7-хлор-4карбокси-2-хинолилальдегид моногидрат (изIn a similar way, 7-chloro-4carboxy-2-quinolylaldehyde monohydrate (from
спирта) с выходом 89,2%, т. пл. 220-221 °С.alcohol) with the release of 89.2%, so pl. 220-221 ° C.
Найдено, %: С 52,12; Н 3,12; N 5,30; С1 13,48.Found,%: C 52.12; H 3.12; N 5.30; C1 13.48.
C H8NO4C1.C H8NO4C1.
Вычислено, %: С 52,08; Н 3,17; N 5,52; С1 13,97.Calculated,%: C, 52.08; H 3.17; N 5.52; C1 13.97.
Пример 2. Гуанилгидразон-4-карбокси-2хинолил альдегида.Example 2. Guanilhydrazone-4-carboxy-2-quinolide aldehyde.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU333168A1 true SU333168A1 (en) |
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