SU186485A1 - - Google Patents
Info
- Publication number
- SU186485A1 SU186485A1 SU1030431A SU1030431A SU186485A1 SU 186485 A1 SU186485 A1 SU 186485A1 SU 1030431 A SU1030431 A SU 1030431A SU 1030431 A SU1030431 A SU 1030431A SU 186485 A1 SU186485 A1 SU 186485A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- keto
- atmosphere
- substituted
- benzyl
- diethylene glycol
- Prior art date
Links
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KASJZXHXXNEULX-UHFFFAOYSA-N 1,5,6,7-tetrahydroindol-4-one Chemical class O=C1CCCC2=C1C=CN2 KASJZXHXXNEULX-UHFFFAOYSA-N 0.000 description 2
- PYDYILSIDWNPMK-UHFFFAOYSA-N 1-benzylindol-4-ol Chemical compound C1=CC=2C(O)=CC=CC=2N1CC1=CC=CC=C1 PYDYILSIDWNPMK-UHFFFAOYSA-N 0.000 description 2
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- -1 1,3-dimethyl-2-carboxy-4-keto-4, 5, 6, 7-tetrahydroindole Chemical compound 0.000 description 1
- RYWYLFSBHZEAJD-UHFFFAOYSA-N 2-hydroxy-6-nitrobenzaldehyde Chemical compound OC1=CC=CC([N+]([O-])=O)=C1C=O RYWYLFSBHZEAJD-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N Nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
СПОСОБ ПОЛУЧЕНИЯ ЗАМЕЩЕННЫХ 4-ОКСИИНДОЛОВMETHOD FOR OBTAINING SUBSTITUTED 4-OXYINDOLS
Изобретение относитс к области получени соединений, которые могут найти применение как физиологически активные вещества.The invention relates to the field of the preparation of compounds which can be used as physiologically active substances.
Известен способ получени 4-оксинндола, заключающийс в том, что 2-окси-6-нитробензальдегид обрабатывают нитрометаном с последующим восстановлением и гидролизом образовавшегос промежуточного продукта.A known method for the preparation of 4-oxindol is that 2-hydroxy-6-nitrobenzaldehyde is treated with nitromethane, followed by reduction and hydrolysis of the resulting intermediate.
С целью использованн легкодоступных исходных веществ предлагаетс способ получени замещенных 4-оксииндолов дегидрированием замещенных или 2,3-незамещенных 4-кето-4, 5, 6, 7-тетрагидроиндолов в присутствии палладированного угл в среде диэтиленгликол и атмосфере COg.For the purpose of using readily available starting materials, a method is proposed for preparing substituted 4-hydroxyindoles by dehydrating substituted or 2,3-unsubstituted 4-keto-4, 5, 6, 7-tetrahydroindoles in the presence of palladium carbon in diethylene glycol and COg atmosphere.
Пример 1. Кип т т 2 г 1,3-диметил-2-карбокси-4-кето-4 , 5, 6, 7-тетрагидроиндола с 1 г 5%-ного палладированного угл в 20 мл диэтиленгликол в атмосфере СО2 в течение 12 час. Реакционную смесь охлаждают и фильтрованием отдел ют катализатор. Прибавл ют двойное количество воды и экстрагируют дважды бензолом. Объединенные бензольные выт жки промывают водой и экстрагируют трижды 20%-ным раствором щелочн. После нейтрализации концентрированной сол ной кислотой в атмосфере СОа получают 0,4 г (20%) 1,3-диметил-2-карбэтокси-4-оксииндола, т. пл. 152°С.Example 1. 2 g of 1,3-dimethyl-2-carboxy-4-keto-4, 5, 6, 7-tetrahydroindole are boiled with 1 g of 5% palladium carbon in 20 ml of diethylene glycol in a CO2 atmosphere for 12 hour. The reaction mixture is cooled and the catalyst is filtered off. Double water is added and extracted twice with benzene. The combined benzene extracts are washed with water and extracted three times with a 20% alkaline solution. After neutralization with concentrated hydrochloric acid in a CO 2 atmosphere, 0.4 g (20%) of 1,3-dimethyl-2-carbethoxy-4-oxyindole is obtained, m.p. 152 ° C.
Найдено, %: С 66,91; 67,07; П 6,20; 6,29.Found,%: C, 66.91; 67.07; P 6.20; 6.29.
Ci3H,503N.Ci3H, 503N.
Вычислено, %: С 66,96; Н 6,48.Calculated,%: C, 66.96; H 6.48.
П р и м е р 2.PRI me R 2.
А. Нагревают 1,75 г 2-карбокси-4-кето-4, о, 6, 7-тетрагидробензофурана с раствором 1,2 г бензиламина в 10 мл этилового спирта в запа нной ампуле в течение 40 час при 150°С. Удал ют в вакууме растворитель и обрабатывают маслообразный остаток гор чим петролейным эфиром. При охлаждении объединенных эфирных выт жек выпадают белые м гкне кристаллы 1-бензил-4-кето-4, 5, 6, 7-тетрагндронндола , 1,5 г (60%), т. пл. 85°С.A. 1.75 g of 2-carboxy-4-keto-4, o, 6,7-tetrahydrobenzofuran with a solution of 1.2 g of benzylamine in 10 ml of ethyl alcohol in a sealed ampoule are heated for 40 hours at 150 ° C. The solvent is removed in vacuo and the oily residue is treated with hot petroleum ether. When the combined ether extracts are cooled, white crystals of 1-benzyl-4-keto-4, 5, 6, 7-tetragndronndol, 1.5 g (60%), t.p. 85 ° C.
Найдено, %: С 79,59; 79,76; Н 6,96; 6,97.Found,%: C 79.59; 79.76; H 6.96; 6.97.
CisHisNO.CisHisNO.
Вычислено, %: С 79,97; Н 6,71.Calculated,%: C 79.97; H 6.71.
Б. Кип т т смесь 1,2 г 1-бензил-4-кето-4, 5, 6, 7-тетрагндроиндола, 1 г 5%-ного паллади на угле и 20 мл диэтиленгликол в атмосфере СО-2 в течение 14 час. Теплый раствор фильтруют дл удалени катализатора, к фильтрату прибавл ют 50 мл воды и экстрагируют бензолом три раза. Объединенные бензольные выт жки промывают несколько раз водой и экстрагируют 20%-ным раствором щелочи. Подкисл ют щелочной раствор концентрированной 3 После удалени растворител и перекристаллизации из петролейного эфира получают 0,3 г ( 25%) 1-бензил-4-оксииндола, т. пл. 95°С. Найдено, %: С 80,54; 80,46; Н 6,03; 6,14. CisHisNO. Вычислено, %: С 80,69; Н 5,87. Гидрирование 1-бензил-4-оксииндола в обычных услови х с 5%-ным палладием на угле приводит к известному 4-оксииндолу. 4 Предмет изобретени Способ получени замещенных 4-оксииндолов , отличающийс тем, что, с целью расширени сырьевой базы, замещенные или 2,3-незамещенные 4-кето-4, 5, 6, 7-тетрагидроиндолы подвергают дегидрированию в присутствии палладированного угл в среде диэтиленгликол в атмосфере СО2.B. Boil a mixture of 1.2 g of 1-benzyl-4-keto-4, 5, 6, 7-tetrahndroindole, 1 g of 5% palladium on carbon and 20 ml of diethylene glycol in a CO-2 atmosphere for 14 hours. . The warm solution is filtered to remove the catalyst, 50 ml of water are added to the filtrate and extracted with benzene three times. The combined benzene extracts are washed several times with water and extracted with a 20% alkali solution. The alkaline solution is acidified with concentrated 3 After removal of the solvent and recrystallization from petroleum ether, 0.3 g (25%) of 1-benzyl-4-hydroxyindole is obtained, m.p. 95 ° C. Found,%: C 80.54; 80.46; H 6.03; 6.14. CisHisNO. Calculated,%: C 80.69; H 5.87. Hydrogenation of 1-benzyl-4-hydroxyindole under ordinary conditions with 5% palladium on charcoal gives the known 4-hydroxyindole. 4 Subject of the invention. A method for producing substituted 4-oxyindoles, characterized in that, in order to expand the raw material base, substituted or 2,3-unsubstituted 4-keto-4, 5, 6, 7-tetrahydroindoles are dehydrated in the presence of palladium carbon in diethylene glycol in the atmosphere of CO2.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU186485A1 true SU186485A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093351A (en) * | 1989-01-05 | 1992-03-03 | Du Pont Merck Pharmaceutical Company | Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093351A (en) * | 1989-01-05 | 1992-03-03 | Du Pont Merck Pharmaceutical Company | Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors |
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