JPS645025B2 - - Google Patents
Info
- Publication number
- JPS645025B2 JPS645025B2 JP56036298A JP3629881A JPS645025B2 JP S645025 B2 JPS645025 B2 JP S645025B2 JP 56036298 A JP56036298 A JP 56036298A JP 3629881 A JP3629881 A JP 3629881A JP S645025 B2 JPS645025 B2 JP S645025B2
- Authority
- JP
- Japan
- Prior art keywords
- hexahydrocarbostyryl
- reaction
- aminocyclohexenone
- acrylic acid
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- ZZMRPOAHZITKBV-UHFFFAOYSA-N 3-aminocyclohex-2-en-1-one Chemical compound NC1=CC(=O)CCC1 ZZMRPOAHZITKBV-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000006356 dehydrogenation reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 3
- MBPQVWGCNCNOQG-UHFFFAOYSA-N 2-aminocyclohex-2-en-1-one Chemical compound NC1=CCCCC1=O MBPQVWGCNCNOQG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XOXGLLQTNQBDKL-UHFFFAOYSA-N 5-hydroxyquinolin-2(1H)-one Chemical compound N1C(=O)C=CC2=C1C=CC=C2O XOXGLLQTNQBDKL-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56036298A JPS57149270A (en) | 1981-03-12 | 1981-03-12 | Preparation of 3,4,5,6,7,8-hexahydrocarbostyril-5-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56036298A JPS57149270A (en) | 1981-03-12 | 1981-03-12 | Preparation of 3,4,5,6,7,8-hexahydrocarbostyril-5-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57149270A JPS57149270A (en) | 1982-09-14 |
| JPS645025B2 true JPS645025B2 (fr) | 1989-01-27 |
Family
ID=12465900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56036298A Granted JPS57149270A (en) | 1981-03-12 | 1981-03-12 | Preparation of 3,4,5,6,7,8-hexahydrocarbostyril-5-one |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57149270A (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5919095B2 (ja) * | 1977-06-22 | 1984-05-02 | 大塚製薬株式会社 | キノリン誘導体及びその製造法 |
-
1981
- 1981-03-12 JP JP56036298A patent/JPS57149270A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57149270A (en) | 1982-09-14 |
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