SU450409A3 - Способ получени 1,4-дигидро1,4-этено-изохинолин-3(2н)-онов - Google Patents
Способ получени 1,4-дигидро1,4-этено-изохинолин-3(2н)-оновInfo
- Publication number
- SU450409A3 SU450409A3 SU1709505A SU1709505A SU450409A3 SU 450409 A3 SU450409 A3 SU 450409A3 SU 1709505 A SU1709505 A SU 1709505A SU 1709505 A SU1709505 A SU 1709505A SU 450409 A3 SU450409 A3 SU 450409A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dihydro
- ones
- mol
- dihydro1
- isoquinoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- -1 1,4-Dihydro-1,4-ethanoisoquinolin3 (2H) -one-9,10-dicarboxylic acid anhydride Chemical compound 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NGAHDYQQDICYJW-UHFFFAOYSA-N 2-methylisoquinolin-3-one Chemical compound C1=CC=CC2=CC(=O)N(C)C=C21 NGAHDYQQDICYJW-UHFFFAOYSA-N 0.000 description 2
- GYPOFOQUZZUVQL-UHFFFAOYSA-N 2h-isoquinolin-3-one Chemical compound C1=CC=C2C=NC(O)=CC2=C1 GYPOFOQUZZUVQL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- IHNINSVQYKIZIC-UHFFFAOYSA-N 2h-quinolin-3-one Chemical compound C1=CC=CC2=CC(=O)CN=C21 IHNINSVQYKIZIC-UHFFFAOYSA-N 0.000 description 1
- NQBZTYJBXWLEQN-UHFFFAOYSA-N 9-azatricyclo[6.2.2.02,7]dodeca-2,4,6,9,11-pentaene Chemical compound C12N=CC(C3=CC=CC=C13)C=C2 NQBZTYJBXWLEQN-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000005895 oxidative decarboxylation reaction Methods 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5021470 | 1970-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU450409A3 true SU450409A3 (ru) | 1974-11-15 |
Family
ID=10455102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1709505A SU450409A3 (ru) | 1970-10-22 | 1971-10-22 | Способ получени 1,4-дигидро1,4-этено-изохинолин-3(2н)-онов |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1378403A (en) * | 1972-06-16 | 1974-12-27 | Ucb Sa | Process for the preparation of 3-2h-isoquinolones |
-
1971
- 1971-10-19 NL NL7114352A patent/NL7114352A/xx unknown
- 1971-10-20 DK DK510171A patent/DK126941B/da unknown
- 1971-10-20 DE DE19712152232 patent/DE2152232A1/de active Pending
- 1971-10-21 IT IT5360671A patent/IT1040524B/it active
- 1971-10-21 FI FI296971A patent/FI49607C/fi active
- 1971-10-21 CA CA125,803A patent/CA956313A/en not_active Expired
- 1971-10-21 SE SE1335471A patent/SE368201B/xx unknown
- 1971-10-21 BE BE774240A patent/BE774240A/xx unknown
- 1971-10-21 CH CH1537371A patent/CH541561A/fr not_active IP Right Cessation
- 1971-10-22 HU HUUI000183 patent/HU162914B/hu unknown
- 1971-10-22 SU SU1709505A patent/SU450409A3/ru active
- 1971-10-22 GB GB1333564D patent/GB1333564A/en not_active Expired
- 1971-10-22 PL PL15117571A patent/PL81482B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU162914B (enrdf_load_stackoverflow) | 1973-04-28 |
| FI49607B (enrdf_load_stackoverflow) | 1975-04-30 |
| FI49607C (fi) | 1975-08-11 |
| BE774240A (fr) | 1972-04-21 |
| GB1333564A (en) | 1973-10-10 |
| DK126941B (da) | 1973-09-03 |
| DE2152232A1 (de) | 1972-04-27 |
| CH541561A (fr) | 1973-09-15 |
| IT1040524B (it) | 1979-12-20 |
| CA956313A (en) | 1974-10-15 |
| NL7114352A (enrdf_load_stackoverflow) | 1972-04-25 |
| PL81482B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| SE368201B (enrdf_load_stackoverflow) | 1974-06-24 |
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