SU771104A1 - Method of preparing amino-n-hydroxyphenanthridones - Google Patents
Method of preparing amino-n-hydroxyphenanthridones Download PDFInfo
- Publication number
- SU771104A1 SU771104A1 SU782689586A SU2689586A SU771104A1 SU 771104 A1 SU771104 A1 SU 771104A1 SU 782689586 A SU782689586 A SU 782689586A SU 2689586 A SU2689586 A SU 2689586A SU 771104 A1 SU771104 A1 SU 771104A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- preparing amino
- hydroxyphenanthridones
- zinc
- formula
- target product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 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 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 6
- 229910052979 sodium sulfide Inorganic materials 0.000 description 4
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- KBBVUKVLBUVPQQ-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=2CC3=CC=CC=C3C=2C=C1)C(=O)O Chemical compound [N+](=O)([O-])C1=C(C=2CC3=CC=CC=C3C=2C=C1)C(=O)O KBBVUKVLBUVPQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XKVIJOJUUAKPQA-UHFFFAOYSA-N fluoro nitroformate Chemical compound [O-][N+](=O)C(=O)OF XKVIJOJUUAKPQA-UHFFFAOYSA-N 0.000 description 1
- -1 hydroxylamino groups Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical compound OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к усов шенствованному способу получени нантридонов, которые наход т пр нение в синтезе азокрасителей и полимеров. В патентной и технической ли туре известен способ получени HO-N-оксифенантридонов общей фо лы Т где Т- - СО, И. NH2,NHOH, заключающийс в том, что флуоре нитрокарбоновую кислоту общей ф лы II NOj.; где R Н, со обрабатывают хлористым оловом при 70-100 0,0 последующим выделением Uc левого продукта известным способом 1. Недостатками известного способа вл ютс низкий выход целевого продукта (45-50% от теоретического) и низкое качество из-за побочных продуктов более полного восстановлени . Целью изобретени вл етс повышение выхода целевого продукта. Поставленна цель достигаетс тем, что нитрофлуоренонкарбоновую кислоту общей формулы обрабатывают сначала раствором сульфида натри при температуре 70-100с, а затем цинком в присутствии электролита хлорида аммони при температуре 80100 С с последующим выделением целевого продукта известным приемом. При обработке сульфидом натри восстанавливаютс Ы02.-группы только в п-положени х к бифенильной св зи до NHj -rpynn, а НОц -группы-в о-положени х остаютс незатронутыми.- При дальнейшей обработке цинком в присутствии электролита восстанавливают оставшиес NO,j -rpynnu до гидроксиламиногрупп с последующей циклизацией и вьеделением продукта известным способом.The invention relates to an improved method for the preparation of nantridones, which are found in the synthesis of azo dyes and polymers. In the patent and technical literature, a method is known for producing HO-N-oxyphenanthridones of a total ploid T where T is CO, I. NH2, NHOH, which means that the fluoro nitrocarboxylic acid of the total II NOj; where R N, co are treated with tin chloride at 70-100 0.0 followed by separation of the Uc left product in a known manner 1. The disadvantages of this method are the low yield of the target product (45-50% of the theoretical) and the poor quality due to by-products more full recovery. The aim of the invention is to increase the yield of the target product. This goal is achieved by the fact that the nitrofluorenecarboxylic acid of the general formula is first treated with sodium sulfide solution at a temperature of 70-100 s and then with zinc in the presence of ammonium chloride electrolyte at a temperature of 80100 ° C, followed by isolation of the target product by a known technique. When treated with sodium sulfide, the N02.-groups are reduced only in the n-positions to the biphenyl bond to NHj-rpynn, and the NOC-groups-in the-positions remain unaffected. - With further zinc treatment in the presence of an electrolyte, the remaining NO, j are reduced. -rpynnu to hydroxylamino groups, followed by cyclization and product separation in a known manner.
Пример . 1 стади . К суспензии 3 вес.ч. нитрокарбоновой кислоты в 50 вес.ч. воды постепенно прибавл ют при 70-lOO C рассчитанное количество 25%-ного раствора сульфида натри Cl/1 1/2г-мол сульфида натри на 1г-моль кислоты из расчета на одну восстанавливаемую нитрогруппу)в течение 20-30 мин и после прибавлени перемешивают 15 мин при этой же температуре. PeaKu OHHsno массу охлаждают до , нейтрализ5пот концентрированной сол ной кислотой.An example. Stage 1 To suspension 3 weight.h. nitrocarboxylic acid in 50 weight.h. water is gradually added at 70-lOO C the calculated amount of a 25% aqueous solution of sodium sulfide Cl / 1 1/2 g-mol sodium sulfide per 1 g-mol acid per one reduced nitro group) for 20-30 minutes and after the addition is stirred 15 min at the same temperature. PeaKu OHHsno mass is cooled to neutralize with concentrated hydrochloric acid.
П стади . В реакционную массу внос т 70 вес.ч. этанола, 1,2 вес.ч. хлорида аммони и 3 вес.ч. технического порошка цинка (из расчета на одну восстанавливаемую нитрогруппу), перемешивают при температуре 80-100 С g- течение 1-2 ч и затем охлаждают.Вьвделившийс осадок цинкового комплекса отдел ют, раствор ют в холодной концентрированной серной кислоте , размешивают 10 мин и затем разбавл ют водой. Отфильтровывают продукт , промывают водой до удалени сульфат-ионов и сушат при . Получают аМино-М-оксифенантридон с выходом 85-90%.P stage. 70 parts by weight are introduced into the reaction mass. ethanol, 1.2 weight.h. ammonium chloride and 3 weight.h. technical zinc powder (based on one reduced nitro group), stirred at a temperature of 80-100 ° C g for 1-2 hours and then cooled. The precipitated zinc complex precipitate is separated, dissolved in cold concentrated sulfuric acid, stirred for 10 minutes and then diluted with water. The product is filtered off, washed with water until the sulfate ions are removed and dried at. Get Minom-M-oxyphenanthridone with the release of 85-90%.
Характеристики амино-N-оксифенантридонов , полученных двухступенчатым способом восстановлени , приведены в таблице.The characteristics of the amino-N-oxyphenanthridones obtained by the two-step reduction method are shown in the table.
CNCN
inin
Ю гоYu go
о оoh oh
го VDth vd
гЛ ОGL O
слcl
ZZ
--
о чoh h
4D чСЧ ОО4D hs oo
Ч- tNW-tN
чоwhat
1Л1L
1Л1L
1Л1L
ЧH
чh
гg
оabout
о чо ч1Лabout cho ch1L
NN
VO VOVO VO
VOVO
гл ch
t о О INt o o in
zz
гОgo
нn
ZZ
NN
оabout
зГ sg
з:оh: o
оabout
о 00 about 00
СО WITH
1Л VO 1L VO
m in kO Tf UDЧ 1Л о аm in kO Tf UDCH 1L oa
txi votxi vo
н оn o
оо го ogo
со о ч- чГ-- Г-Ч Чwith about h chGG-- GHH
fo гоfo go
о -1about -1
41 чУЭ VD VD VD41 CHUE VD VD VD
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782689586A SU771104A1 (en) | 1978-11-27 | 1978-11-27 | Method of preparing amino-n-hydroxyphenanthridones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782689586A SU771104A1 (en) | 1978-11-27 | 1978-11-27 | Method of preparing amino-n-hydroxyphenanthridones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU771104A1 true SU771104A1 (en) | 1980-10-15 |
Family
ID=20795666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782689586A SU771104A1 (en) | 1978-11-27 | 1978-11-27 | Method of preparing amino-n-hydroxyphenanthridones |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU771104A1 (en) |
-
1978
- 1978-11-27 SU SU782689586A patent/SU771104A1/en active
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