SU376373A1 - METHOD OF OBTAINING 5,7-DINITRO-1,2-DIHYDRO-ISOCHI- - Google Patents
METHOD OF OBTAINING 5,7-DINITRO-1,2-DIHYDRO-ISOCHI-Info
- Publication number
- SU376373A1 SU376373A1 SU1633262A SU1633262A SU376373A1 SU 376373 A1 SU376373 A1 SU 376373A1 SU 1633262 A SU1633262 A SU 1633262A SU 1633262 A SU1633262 A SU 1633262A SU 376373 A1 SU376373 A1 SU 376373A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dinitro
- obtaining
- isochi
- dihydro
- ppm
- Prior art date
Links
Description
1one
Изобретение относитс к снособу получени нового производного изохинолина-5,7-динитро-1 ,2-дигидроизохинолона-1, которое может найти применение в качестве полупродукта в синтезе биологически активных веществ.This invention relates to a procedure for the preparation of a new isoquinoline-5,7-dinitro-1, 2-dihydroisoquinolone-1 derivative, which can be used as an intermediate in the synthesis of biologically active substances.
Известно получение 4-полипитрофенилпроизводных 2,6-диметил-2,6-диазагептадиена-2,4 из ароматических полинитросоединений, диметилформамида и хлорокиси фосфора (реакци Вильсмайера).The preparation of 4-polypitrophenyl derivatives of 2,6-dimethyl-2,6-diazaheptadiene-2.4 is known from aromatic polynitro compounds, dimethylformamide and phosphorus oxychloride (Vilsmeier reaction).
Предлагаемый способ заключаетс во взаимодействии 2-метил-3,5-динитробепзойпой кислоты или ее хлораигидрида с диметилформамидом и хлорокисыо фосфора, соировождающемс циклизацией, и выделении целевого продукта известными приемами.The proposed method consists in the interaction of 2-methyl-3,5-dinitrobenzoic acid or its chlorohydride with dimethylformamide and chloroxyso-phosphorus, which is combined with cyclization, and the isolation of the target product by known methods.
Подобиой циклизации в услови х реакции Вильсмайера дл производных изохинолина в литературе ие описано.Similar cyclization under the Vilsmeier reaction conditions for isoquinoline derivatives is not described in the literature.
П р и м е р. Смешивают при комнатной температуре 5,65 г 2-метил-3,5-дипитробензойно кислоты, 27,5 г диметилформамида и 11,5 г РОСЬ, нагревают до 100°С и выдерживают 4 час при этой температуре. Полученный раствор выливают в смесь льда с водой и получают 4,8 г 5,7-дипитро-Ы-метилдигидроизохинолина-1 , т. нл. 222-225°С (СПзМОа или 50о/она HNOa).PRI me R. 5.65 g of 2-methyl-3,5-dipitrobenzoic acid, 27.5 g of dimethylformamide and 11.5 g of POC are mixed at room temperature, heated to 100 ° C and kept at this temperature for 4 hours. The resulting solution was poured into a mixture of ice and water, and 4.8 g of 5,7-dipitro-L-methyldihydroisoquinoline-1, t. Nl, were obtained. 222-225 ° C (SPZMOa or 50 ° / HNOa).
Найдено, %: С 47,66 47,64; П 3,14, 3,10; N 16,30; 16,32.Found,%: C 47.66 47.64; P 3.14, 3.10; N 16.30; 16.32.
CioHrNaOs.CioHrNaOs.
Вычислено, %: С 48,19; Н 2,81; N 16,37.Calculated,%: C 48.19; H 2.81; N 16.37.
Строение получепного продукта установлено методами И К- и ПМР-спектроскопии.The structure of the obtained product was established by the methods of K and PMR spectroscopy.
В ИК-спектре отсутствуют полосы поглощени , характерные дл карбонильной группы. ПМР-спектр, сн тый на частоте 60 }лгц в дейтерохлорформе относительно тетраметилсилана , как внутреннего эталопа, состоит из двух систем типа АВ в ароматической области и синглета при 3,70 м. д., который отнесеи к N-СНз-группе. Сигналы при 7,37 м. д. и 9,57 м.д. (имеетс дополнительное спиновое расщепление 0,6 zii) отнесены к протонам в положени х 4 и 8. Дублет нри 9,20 м. д. (расщепление 2,6 ai() отнесен к Не, а дублет при 7,50 м. д. (рас1цепление 7,5 гц} к Пз. Ин1тегральные интенсивности спектральных линий соответствуют предполагаемо) структуре соединени .In the IR spectrum, there are no absorption bands characteristic of the carbonyl group. The PMR spectrum, taken at a frequency of 60} lgc in deuterium chloroform relative to tetramethylsilane, as an internal reference, consists of two systems of the AB type in the aromatic region and a singlet at 3.70 ppm, which is referred to the N-СНз-group. Signals at 7.37 ppm and 9.57 ppm (there is an additional spin splitting of 0.6 zii) attributed to protons at positions 4 and 8. The doublet at 9.20 ppm (the splitting of 2.6 ai () is attributed to He, and the doublet at 7.50 ppm . (ramping of 7.5 Hz} to Pz. The integral intensities of the spectral lines are supposed to correspond) to the structure of the compound.
Предмет изобретени Subject invention
Способ получени 5,7-динитро-1,2-дигидроизохииолона-1 , отличающийс тем, что 2-метил-3 ,5-динитробензойцую кислоту или ее хлораигидрид обрабатывают диметилформамидом и хлорокисью фосфора с последующим выделением целевого продукта известным способом .The method of obtaining 5,7-dinitro-1,2-dihydroisohioolone-1, characterized in that 2-methyl-3, 5-dinitrobenzoic acid or its chlorohydride is treated with dimethylformamide and phosphorus oxychloride, followed by isolation of the target product in a known manner.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1633262A SU376373A1 (en) | 1971-03-17 | 1971-03-17 | METHOD OF OBTAINING 5,7-DINITRO-1,2-DIHYDRO-ISOCHI- |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1633262A SU376373A1 (en) | 1971-03-17 | 1971-03-17 | METHOD OF OBTAINING 5,7-DINITRO-1,2-DIHYDRO-ISOCHI- |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU376373A1 true SU376373A1 (en) | 1973-04-05 |
Family
ID=20468754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1633262A SU376373A1 (en) | 1971-03-17 | 1971-03-17 | METHOD OF OBTAINING 5,7-DINITRO-1,2-DIHYDRO-ISOCHI- |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU376373A1 (en) |
-
1971
- 1971-03-17 SU SU1633262A patent/SU376373A1/en active
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