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)
Abstract
Description
Zatímco dříve popsaný postup je možno úspěšně použít pro práci v malém měřítku» není použití výše zmíněného oxidačního činidla vhodně pro práci v průmyslovém měřítku· Manganistan draselný je totiž vysoce toxický a nebezpečný a oxid manganičitý, vzni-While the previously described process can be successfully used for small scale work »the use of the above oxidizing agent is not suitable for industrial scale work. Potassium permanganate is very toxic and dangerous and manganese
Ka^cí při reakci jako vedlejší produkt» vyžaduje nákladné skladování a manipulaci·The reaction by-product requires expensive storage and handling.
Předložený vynález popisuje a chrání zlepšený způsob výroby 5-alkyl-2-pyrazinkarboxylové kyseliny·The present invention describes and protects an improved process for producing 5-alkyl-2-pyrazinecarboxylic acid.
Podle vynálezu ee 5-alkyl~2-pyrazinkarbo- .According to the invention, 5-alkyl-2-pyrazinecarbo-.
xylová kyselina obecného vzorce I může vyrábět tím» že se nitril diaminomaleinové kyseliny vzorce IIThe xylic acid of formula (I) can be produced by reacting a diaminomaleic acid nitrile of formula (II)
226 741 (И) kondenzuje se sloučeninou obecného vzorce226,741 (I) condenses with a compound of formula
CHOCO^ v němžCHOCO ^ in which
R-^ mé shora uvedený význam, v polárním rozpouštědle při teplotě od 35 do 85 °C a získaná sloučenina obecného vzorce IIIR is as defined above, in a polar solvent at a temperature of from 35 to 85 ° C and the compound of formula III obtained
(III) v němž(III) in which:
R·^ má shora uvedený význam, se nechá reagovat a kyselinou v polárním rozpouštědle při teplotě od 85 do 100 °C.R 6 is as defined above, is reacted with an acid in a polar solvent at a temperature of from 85 to 100 ° C.
226 741226 741
Vhodnými rozpouštědly pro kondenzaci nitrilu diaminomleinové kyseliny s glyoxalem nebo s a-ketoaddhy/dem jsou voda, alkohol s 1 až 6 atomy uhlíku nebo jejich směsi. Kondeenační reakce se provádí výhodně v přítomnnssi kyseliny*Suitable solvents for the condensation of diaminomleic acid nitrile with glyoxal or α-ketoaddhyde are water, a C 1 -C 6 alcohol or mixtures thereof. The condensation reaction is preferably carried out in the presence of an acid.
Reakce dikyanpyrazinu ' vzorce III s kyselinou skýtá zcela překvapivě pouze sloučeninu obecného vzorce It Vhodnými kyselinami jsou kyselina sírová, kyselina methannuLionová, ^šedina fosforečná, kyselina trifluoraethansulfonová i kyselina chlorovodíková. Vhodným rozpouštědlem je voda. Účelně činí koncentrace ^šediny 30 až 50 %· · Sloučeniny vzorce I jsou cennými výchozími látkami pro výrobu pyrazin-^oxidů, které mjí hypooipomLcko-u i hypoglykemickou účinnoot, i které jsou prosty *Surprisingly, the reaction of the dicyanopyrazine (III) with an acid affords only the compound of the formula (I). Suitable acids are sulfuric acid, methanonic acid, phosphoric acid, trifluoroethanesulfonic acid and hydrochloric acid. A suitable solvent is water. Conveniently, the concentration of gray is 30 to 50%. The compounds of formula I are valuable starting materials for the production of pyrazine oxides, which have both hypoxipomycin and hypoglycemic activity and which are free of pyrazine oxides.
vedlejších účinků derivátů pyridinu, jak se' popisují %side effects of pyridine derivatives as described by%
v čs. patentním spise č. 172 972.in MS. No. 172,972.
Následnici příklad vynález blíže objasňuje, aniž by jeho rozsah nějakým způsobem omezoval.The following example illustrates the invention in more detail without limiting its scope.
P ř í k 1 a 4Examples 1 and 4
226 741226 741
a) 170 g (10% roztok ve vodě (hmotnoet/objem)) aldehydu kyseliny pyrthrtzoové se přikape za ráchání a . při teplotě matnosti k suspenzi 100 g oÍtriiu- dLaránojmaeioové ^seliny ve směsi 800 mi vody, 900' mi ethaoolu a 45 ml octové kyseliny. Po - 20 minutách je rozpouštění ukončeno· Teplota se zvýší oa 80 °C a v ráchání se - pokračuje dalších 30 minut·(a) 170 g (10% solution in water (w / v)) of pyrthrtzoic acid aldehyde is added dropwise while stirring; and. at a matt temperature to a suspension of 100 g of triturate-dicarboxylic acid in a mixture of 800 ml of water, 900 ml of ethanol and 45 ml of acetic acid. After - 20 minutes the dissolution is complete · The temperature is raised by 80 ° C and the rinsing is continued for 30 minutes ·
Potom se reakční směs - ochladí op 0 °C a produkt' se izoluje filtrací· Po promni vodou až do neutrální reakce a po vysušení se získá 112 g surového ‘ . i—Thereafter, the reaction mixture is cooled to 0 DEG C. and the product is isolated by filtration. After the reaction is carried out with water until neutral, 112 g of crude product is obtained after drying. and-
S^ydikyan-e-hethyrpyrmzinu, teplota tání 98 ažHO °C·Sodium cyanopyridine, m.p. 98 DEG-10 DEG C.
NMR spektrum (deuteriaováný chloroform) z tetrimethy1· siianu: 2,8 β (s, CH^), 8,85 (s, prtmapický proton)·NMR spectrum (deuterated chloroform) of tetrimethylsian: 2.8 β (s, CH 2), 8.85 (s, prtmap proton) ·
b) Suspenze 10 g surového 2,3-dikedn-5-met½rlpyrpziou získaná způsobem popsaným v odstavci a) ve 100 rá kyseliny sírové )50% vodný roztok (objem/objem)) se udržuje 3- hodiny za ráchárá při teplotě 100 °C· Pftom se reakční směs ochladí přidáním 100 g rozmělněného ledu a přidáním 270 ml vodného roztoku hydroxidu - sodného (20% roztok (hmotnott/objsm)) se hodnota pH upraví op 1·(b) A suspension of 10 g of crude 2,3-dikedene-5-methylpyrimidium obtained as described in (a) in 100% sulfuric acid) 50% aqueous solution (v / v) is maintained for 3 hours at 100 ° C. The reaction mixture is then cooled by the addition of 100 g of crushed ice and the pH is adjusted again by adding 270 ml of aqueous sodium hydroxide solution (20% w / v).
226 741226 741
Vodná fáze se extrahuje me ttylethylketonem· Extrakty se spojí a promji se až do neutrální reakce nasyceným roztokem chloridu sodného· Odpptfením rozpouštědla ve vakuu se získá pevný zbytek, který krystaluje z vody· Získá se 6 g 5-m^t^lh^y^*2^pyrazi^nkarboxylové tyseliny ' o ' teplotě tání 163 až 167 °C·The aqueous phase is extracted with methyl ethyl ketone. The extracts are combined and washed until neutral with saturated sodium chloride solution. The solvent is evaporated off under vacuum to give a solid residue which crystallizes from water. 163 DEG-167 DEG C. 2-Pyrazinecarboxylic acid;
NMR spektrum (deuteri z ováný chloroform) z tetramettylsilanu» 2,8 $ (s, 8,9> 9,3 C^C2 s, aromatické proton),' 10,8 (s, COOH)·NMR spectrum (deutero chloroform from nostrils) of tetramettyl to ila n u »$ 2.8 (s, 8.9> 9.3 C ^ C 2 s, aromatic-H) '10.8 (s, COOH) ·
Claims (4)
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)
| Country | Link |
|---|---|
| JP (1) | JPS57200368A (en) |
| AT (1) | AT387217B (en) |
| AU (1) | AU8412682A (en) |
| BE (1) | BE893317A (en) |
| CA (1) | CA1237724A (en) |
| CH (1) | CH649763A5 (en) |
| CS (1) | CS226741B2 (en) |
| DE (1) | DE3219407A1 (en) |
| DK (1) | DK155325C (en) |
| FI (1) | FI73669C (en) |
| FR (1) | FR2506768B1 (en) |
| GR (1) | GR76417B (en) |
| HU (1) | HU187716B (en) |
| IE (1) | IE52992B1 (en) |
| IL (1) | IL65864A (en) |
| IT (1) | IT1210478B (en) |
| NL (1) | NL8202105A (en) |
| SE (1) | SE462971B (en) |
| YU (1) | YU42766B (en) |
| ZA (1) | ZA823660B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1201417B (en) * | 1985-05-17 | 1989-02-02 | Montedison Spa | PROCEDURE FOR THE PREPARATION OF 2-CARBOXYPYRAZINE 4 OXIDE |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU470007B2 (en) * | 1972-04-28 | 1976-02-26 | Farmitalia Carlo Erba S.R.L. | Pyrazine 4-oxide derivatives and process for their preparation |
| JPS565742B2 (en) * | 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 |
| JPS5488281A (en) * | 1977-12-20 | 1979-07-13 | Nitsupou Kagaku Kk | Manufacture of pyrazine monocarboxylic acid |
| JPS5488280A (en) * | 1977-12-20 | 1979-07-13 | Nitsupou Kagaku Kk | Manufacture of dicyanopyradines |
-
1982
- 1982-05-21 NL NL8202105A patent/NL8202105A/en active Search and Examination
- 1982-05-24 FI FI821832A patent/FI73669C/en not_active IP Right Cessation
- 1982-05-24 DE DE19823219407 patent/DE3219407A1/en active Granted
- 1982-05-24 AT AT0203682A patent/AT387217B/en not_active IP Right Cessation
- 1982-05-24 IL IL65864A patent/IL65864A/en not_active IP Right Cessation
- 1982-05-25 AU AU84126/82A patent/AU8412682A/en not_active Abandoned
- 1982-05-25 FR FR8209038A patent/FR2506768B1/en not_active Expired
- 1982-05-25 CS CS823842A patent/CS226741B2/en unknown
- 1982-05-25 GR GR68246A patent/GR76417B/el unknown
- 1982-05-25 CA CA000403636A patent/CA1237724A/en not_active Expired
- 1982-05-26 IE IE1261/82A patent/IE52992B1/en not_active IP Right Cessation
- 1982-05-26 JP JP57088153A patent/JPS57200368A/en active Granted
- 1982-05-26 ZA ZA823660A patent/ZA823660B/en unknown
- 1982-05-26 SE SE8203273A patent/SE462971B/en not_active IP Right Cessation
- 1982-05-27 IT IT8221517A patent/IT1210478B/en active Protection Beyond IP Right Term
- 1982-05-27 BE BE0/208187A patent/BE893317A/en not_active IP Right Cessation
- 1982-05-27 HU HU821712A patent/HU187716B/en unknown
- 1982-05-27 CH CH3285/82A patent/CH649763A5/en not_active IP Right Cessation
- 1982-05-27 DK DK239482A patent/DK155325C/en not_active IP Right Cessation
- 1982-05-27 YU YU1131/82A patent/YU42766B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR76417B (en) | 1984-08-10 |
| JPH0456034B2 (en) | 1992-09-07 |
| IT1210478B (en) | 1989-09-14 |
| FR2506768A1 (en) | 1982-12-03 |
| FI821832A0 (en) | 1982-05-24 |
| AT387217B (en) | 1988-12-27 |
| YU42766B (en) | 1988-12-31 |
| CA1237724A (en) | 1988-06-07 |
| FI73669C (en) | 1987-11-09 |
| DK239482A (en) | 1982-11-29 |
| IT8221517A0 (en) | 1982-05-27 |
| NL8202105A (en) | 1982-12-16 |
| BE893317A (en) | 1982-11-29 |
| CH649763A5 (en) | 1985-06-14 |
| DK155325C (en) | 1989-09-18 |
| FI73669B (en) | 1987-07-31 |
| JPS57200368A (en) | 1982-12-08 |
| HU187716B (en) | 1986-02-28 |
| ATA203682A (en) | 1988-05-15 |
| ZA823660B (en) | 1983-03-30 |
| AU8412682A (en) | 1982-12-02 |
| DE3219407A1 (en) | 1983-01-05 |
| SE462971B (en) | 1990-09-24 |
| IL65864A (en) | 1985-08-30 |
| IE821261L (en) | 1982-11-28 |
| DE3219407C2 (en) | 1990-09-06 |
| FR2506768B1 (en) | 1985-06-21 |
| YU113182A (en) | 1985-03-20 |
| DK155325B (en) | 1989-03-28 |
| IE52992B1 (en) | 1988-04-27 |
| IL65864A0 (en) | 1982-08-31 |
| SE8203273L (en) | 1982-11-29 |
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