SU528869A3 - Способ получени производных изоиндолина или их солей - Google Patents
Способ получени производных изоиндолина или их солейInfo
- Publication number
- SU528869A3 SU528869A3 SU1683466A SU1683466A SU528869A3 SU 528869 A3 SU528869 A3 SU 528869A3 SU 1683466 A SU1683466 A SU 1683466A SU 1683466 A SU1683466 A SU 1683466A SU 528869 A3 SU528869 A3 SU 528869A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dihydro
- dibenzo
- cyclohepten
- spiro
- substituents
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 9
- -1 methoxy- Chemical class 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 238000010992 reflux Methods 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 239000007789 gas Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000012298 atmosphere Substances 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000011261 inert gas Substances 0.000 claims 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 2
- 150000004681 metal hydrides Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- 102000020897 Formins Human genes 0.000 claims 1
- 108091022623 Formins Proteins 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 244000007853 Sarothamnus scoparius Species 0.000 claims 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 235000014633 carbohydrates Nutrition 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5459770A | 1970-07-13 | 1970-07-13 | |
| US12209271A | 1971-03-08 | 1971-03-08 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1843948A Division SU493964A3 (ru) | 1970-07-13 | 1971-07-12 | Способ производных изоиндолина или их солей |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU528869A3 true SU528869A3 (ru) | 1976-09-15 |
Family
ID=26733244
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1843948A SU493964A3 (ru) | 1970-07-13 | 1971-07-12 | Способ производных изоиндолина или их солей |
| SU1683466A SU528869A3 (ru) | 1970-07-13 | 1971-07-12 | Способ получени производных изоиндолина или их солей |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1843948A SU493964A3 (ru) | 1970-07-13 | 1971-07-12 | Способ производных изоиндолина или их солей |
Country Status (14)
-
1971
- 1971-07-02 CH CH976271A patent/CH554330A/xx not_active IP Right Cessation
- 1971-07-05 NL NL7109248A patent/NL7109248A/xx unknown
- 1971-07-09 DD DD16303371A patent/DD97886A5/xx unknown
- 1971-07-09 GB GB3227771A patent/GB1355977A/en not_active Expired
- 1971-07-09 DE DE19712134396 patent/DE2134396A1/de active Pending
- 1971-07-12 PL PL14939171A patent/PL85094B1/pl unknown
- 1971-07-12 SU SU1843948A patent/SU493964A3/ru active
- 1971-07-12 ES ES393180A patent/ES393180A1/es not_active Expired
- 1971-07-12 AT AT604371A patent/AT325603B/de not_active IP Right Cessation
- 1971-07-12 CA CA117,958A patent/CA954511A/en not_active Expired
- 1971-07-12 SU SU1683466A patent/SU528869A3/ru active
- 1971-07-12 AU AU31126/71A patent/AU462870B2/en not_active Expired
- 1971-07-12 BE BE769901A patent/BE769901A/xx unknown
- 1971-07-12 SE SE898971A patent/SE376610B/xx unknown
- 1971-07-13 FR FR7125569A patent/FR2100895B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA604371A (de) | 1975-01-15 |
| CA954511A (en) | 1974-09-10 |
| AT325603B (de) | 1975-10-27 |
| AU462870B2 (en) | 1975-07-10 |
| SE376610B (enrdf_load_stackoverflow) | 1975-06-02 |
| FR2100895B1 (enrdf_load_stackoverflow) | 1975-12-26 |
| DE2134396A1 (de) | 1972-02-10 |
| GB1355977A (en) | 1974-06-12 |
| ES393180A1 (es) | 1974-09-01 |
| PL85094B1 (enrdf_load_stackoverflow) | 1976-04-30 |
| FR2100895A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| BE769901A (enrdf_load_stackoverflow) | 1972-01-12 |
| CH554330A (de) | 1974-09-30 |
| NL7109248A (enrdf_load_stackoverflow) | 1972-01-17 |
| AU3112671A (en) | 1973-01-18 |
| DD97886A5 (enrdf_load_stackoverflow) | 1973-05-20 |
| SU493964A3 (ru) | 1975-11-28 |
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