CS226741B2 - Method of preparing 5-alkyl-2-pyrazinecarboxylic acid - Google Patents
Method of preparing 5-alkyl-2-pyrazinecarboxylic acid Download PDFInfo
- Publication number
- CS226741B2 CS226741B2 CS823842A CS384282A CS226741B2 CS 226741 B2 CS226741 B2 CS 226741B2 CS 823842 A CS823842 A CS 823842A CS 384282 A CS384282 A CS 384282A CS 226741 B2 CS226741 B2 CS 226741B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- formula
- alkyl
- group
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- OTVZGAXESBAAQQ-UHFFFAOYSA-N pyrazine-2,3-dicarbonitrile Chemical compound N#CC1=NC=CN=C1C#N OTVZGAXESBAAQQ-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 4
- -1 diaminomaleic acid nitrile Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229940015043 glyoxal Drugs 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 2
- 150000003222 pyridines Chemical class 0.000 abstract description 2
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 abstract 2
- 150000003216 pyrazines Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RUIZBQQGWNBRFH-UHFFFAOYSA-N 1-oxidopyrazin-1-ium Chemical class [O-][N+]1=CC=NC=C1 RUIZBQQGWNBRFH-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 description 1
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8116263 | 1981-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226741B2 true CS226741B2 (en) | 1984-04-16 |
Family
ID=10522093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS823842A CS226741B2 (en) | 1981-05-28 | 1982-05-25 | Method of preparing 5-alkyl-2-pyrazinecarboxylic acid |
Country Status (20)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1201417B (it) * | 1985-05-17 | 1989-02-02 | Montedison Spa | Procedimento per la preparazione di 2-carbossipirazine 4 ossido |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1361967A (en) * | 1972-04-28 | 1974-07-30 | Erba Carlo Spa | Pyrazine 4-oxide derivatives and process for their preparation |
| JPS565742B2 (enrdf_load_stackoverflow) * | 1973-09-29 | 1981-02-06 | ||
| JPS5134175A (en) * | 1974-09-18 | 1976-03-23 | Sagami Chem Res | Pirajinjudotai no seizohoho |
| JPS52153980A (en) * | 1976-06-17 | 1977-12-21 | Nippon Soda Co Ltd | Synthesis of 2,3-dicyanopyrazine |
| JPS5488280A (en) * | 1977-12-20 | 1979-07-13 | Nitsupou Kagaku Kk | Manufacture of dicyanopyradines |
| JPS5488281A (en) * | 1977-12-20 | 1979-07-13 | Nitsupou Kagaku Kk | Manufacture of pyrazine monocarboxylic acid |
-
1982
- 1982-05-21 NL NL8202105A patent/NL8202105A/nl active Search and Examination
- 1982-05-24 DE DE19823219407 patent/DE3219407A1/de active Granted
- 1982-05-24 IL IL65864A patent/IL65864A/xx not_active IP Right Cessation
- 1982-05-24 AT AT0203682A patent/AT387217B/de not_active IP Right Cessation
- 1982-05-24 FI FI821832A patent/FI73669C/fi not_active IP Right Cessation
- 1982-05-25 CS CS823842A patent/CS226741B2/cs unknown
- 1982-05-25 FR FR8209038A patent/FR2506768B1/fr not_active Expired
- 1982-05-25 GR GR68246A patent/GR76417B/el unknown
- 1982-05-25 CA CA000403636A patent/CA1237724A/en not_active Expired
- 1982-05-25 AU AU84126/82A patent/AU8412682A/en not_active Abandoned
- 1982-05-26 SE SE8203273A patent/SE462971B/sv not_active IP Right Cessation
- 1982-05-26 JP JP57088153A patent/JPS57200368A/ja active Granted
- 1982-05-26 ZA ZA823660A patent/ZA823660B/xx unknown
- 1982-05-26 IE IE1261/82A patent/IE52992B1/en not_active IP Right Cessation
- 1982-05-27 YU YU1131/82A patent/YU42766B/xx unknown
- 1982-05-27 DK DK239482A patent/DK155325C/da not_active IP Right Cessation
- 1982-05-27 HU HU821712A patent/HU187716B/hu unknown
- 1982-05-27 BE BE0/208187A patent/BE893317A/fr not_active IP Right Cessation
- 1982-05-27 CH CH3285/82A patent/CH649763A5/de not_active IP Right Cessation
- 1982-05-27 IT IT8221517A patent/IT1210478B/it active Protection Beyond IP Right Term
Also Published As
| Publication number | Publication date |
|---|---|
| AU8412682A (en) | 1982-12-02 |
| BE893317A (fr) | 1982-11-29 |
| SE8203273L (sv) | 1982-11-29 |
| FI821832A0 (fi) | 1982-05-24 |
| IT1210478B (it) | 1989-09-14 |
| FI73669B (fi) | 1987-07-31 |
| NL8202105A (nl) | 1982-12-16 |
| JPH0456034B2 (enrdf_load_stackoverflow) | 1992-09-07 |
| ATA203682A (de) | 1988-05-15 |
| CA1237724A (en) | 1988-06-07 |
| IT8221517A0 (it) | 1982-05-27 |
| DK155325C (da) | 1989-09-18 |
| SE462971B (sv) | 1990-09-24 |
| HU187716B (en) | 1986-02-28 |
| IL65864A0 (en) | 1982-08-31 |
| YU113182A (en) | 1985-03-20 |
| AT387217B (de) | 1988-12-27 |
| FI73669C (fi) | 1987-11-09 |
| IE821261L (en) | 1982-11-28 |
| CH649763A5 (de) | 1985-06-14 |
| FR2506768B1 (fr) | 1985-06-21 |
| IE52992B1 (en) | 1988-04-27 |
| FR2506768A1 (fr) | 1982-12-03 |
| YU42766B (en) | 1988-12-31 |
| DK239482A (da) | 1982-11-29 |
| GR76417B (enrdf_load_stackoverflow) | 1984-08-10 |
| DK155325B (da) | 1989-03-28 |
| IL65864A (en) | 1985-08-30 |
| DE3219407C2 (enrdf_load_stackoverflow) | 1990-09-06 |
| ZA823660B (en) | 1983-03-30 |
| JPS57200368A (en) | 1982-12-08 |
| DE3219407A1 (de) | 1983-01-05 |
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