DE2108046A1 - Verfahren zur Herstellung von I Alkyl 1,8 naphthyndinderivaten - Google Patents
Verfahren zur Herstellung von I Alkyl 1,8 naphthyndinderivatenInfo
- Publication number
- DE2108046A1 DE2108046A1 DE19712108046 DE2108046A DE2108046A1 DE 2108046 A1 DE2108046 A1 DE 2108046A1 DE 19712108046 DE19712108046 DE 19712108046 DE 2108046 A DE2108046 A DE 2108046A DE 2108046 A1 DE2108046 A1 DE 2108046A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- alkyl
- methyl
- pyridyl
- acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 title description 2
- 125000004957 naphthylene group Chemical group 0.000 title 1
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 13
- -1 (2-pyridyl) aminomethylene Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KDFNZGJPRXHVKR-UHFFFAOYSA-N 6-ethyl-n-methylpyridin-2-amine Chemical compound CCC1=CC=CC(NC)=N1 KDFNZGJPRXHVKR-UHFFFAOYSA-N 0.000 description 2
- PLIBVNHIITWTHE-UHFFFAOYSA-N 6-methyl-2-propylpyridin-3-amine Chemical compound CCCc1nc(C)ccc1N PLIBVNHIITWTHE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PFVYSURSVXECJA-UHFFFAOYSA-N n,6-dimethylpyridin-2-amine Chemical compound CNC1=CC=CC(C)=N1 PFVYSURSVXECJA-UHFFFAOYSA-N 0.000 description 2
- ZUCJRARGRJUOMC-UHFFFAOYSA-N n-ethyl-6-methylpyridin-2-amine Chemical compound CCNC1=CC=CC(C)=N1 ZUCJRARGRJUOMC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- FIQGPIHRUIEFQF-UHFFFAOYSA-N 1,7-dimethyl-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(=O)C=2C1=NC(C)=CC=2 FIQGPIHRUIEFQF-UHFFFAOYSA-N 0.000 description 1
- BUOYIVWFYYMLTR-UHFFFAOYSA-N 1-butyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C(CCC)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)O BUOYIVWFYYMLTR-UHFFFAOYSA-N 0.000 description 1
- DTFBBVDDPVULMK-UHFFFAOYSA-N 2-(aminomethylidene)propanedioic acid Chemical compound NC=C(C(O)=O)C(O)=O DTFBBVDDPVULMK-UHFFFAOYSA-N 0.000 description 1
- DJDDYWYYTKNZPM-UHFFFAOYSA-N 2-amino-1,3-dioxane-4,6-dione Chemical compound NC1OC(=O)CC(=O)O1 DJDDYWYYTKNZPM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLOHMQHLGKHMRW-UHFFFAOYSA-N diethyl 2-[[methyl-(6-methylpyridin-2-yl)amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CN(C)C1=CC=CC(C)=N1 ZLOHMQHLGKHMRW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UYEKHNCKLMEBRX-UHFFFAOYSA-N n,6-diethylpyridin-2-amine Chemical compound CCNC1=CC=CC(CC)=N1 UYEKHNCKLMEBRX-UHFFFAOYSA-N 0.000 description 1
- CEZGMNBAYVZGBA-UHFFFAOYSA-N n-decyl-6-methylpyridin-2-amine Chemical compound CCCCCCCCCCNC1=CC=CC(C)=N1 CEZGMNBAYVZGBA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1501570 | 1970-02-20 | ||
| JP1501670 | 1970-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2108046A1 true DE2108046A1 (de) | 1971-10-07 |
Family
ID=26351078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712108046 Pending DE2108046A1 (de) | 1970-02-20 | 1971-02-19 | Verfahren zur Herstellung von I Alkyl 1,8 naphthyndinderivaten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3813406A (enExample) |
| BE (1) | BE762804A (enExample) |
| CA (1) | CA949578A (enExample) |
| CH (1) | CH550800A (enExample) |
| DE (1) | DE2108046A1 (enExample) |
| FR (1) | FR2078846A5 (enExample) |
| GB (1) | GB1338023A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49270A (enExample) * | 1972-04-20 | 1974-01-05 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU165504B (enExample) * | 1972-02-10 | 1974-09-28 | ||
| US3853864A (en) * | 1972-12-07 | 1974-12-10 | American Home Prod | 1,7-dialkyl-1,2-dihydro-4-hydroxy-1,8-naphthyridine-3-carboxylic acid alkyl esters |
| US3895017A (en) * | 1973-02-20 | 1975-07-15 | Sterling Drug Inc | 3-Acetyl-1-alkyl-1,4-dihydro-4-oxo-1,8-naphthyridines and intermediates |
| JPS6011913B2 (ja) * | 1977-12-27 | 1985-03-28 | 広栄化学工業株式会社 | １，８−ナフチリジン誘導体ならびにその製造方法 |
-
1971
- 1971-02-11 BE BE762804A patent/BE762804A/xx unknown
- 1971-02-12 CA CA105,230A patent/CA949578A/en not_active Expired
- 1971-02-18 US US00097411A patent/US3813406A/en not_active Expired - Lifetime
- 1971-02-19 FR FR7105757A patent/FR2078846A5/fr not_active Expired
- 1971-02-19 DE DE19712108046 patent/DE2108046A1/de active Pending
- 1971-02-22 CH CH253871A patent/CH550800A/xx not_active IP Right Cessation
- 1971-04-19 GB GB2233071A patent/GB1338023A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49270A (enExample) * | 1972-04-20 | 1974-01-05 |
Also Published As
| Publication number | Publication date |
|---|---|
| US3813406A (en) | 1974-05-28 |
| FR2078846A5 (enExample) | 1971-11-05 |
| CH550800A (de) | 1974-06-28 |
| BE762804A (fr) | 1971-08-11 |
| CA949578A (en) | 1974-06-18 |
| GB1338023A (en) | 1973-11-21 |
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