SE441743B - Forfarande for framstellning av 4-(2?721-nitrofenyl)-2,6-dimetyl-3,5-dikarbometoxi-1,4-dihydropyridin - Google Patents
Forfarande for framstellning av 4-(2?721-nitrofenyl)-2,6-dimetyl-3,5-dikarbometoxi-1,4-dihydropyridinInfo
- Publication number
- SE441743B SE441743B SE8204658A SE8204658A SE441743B SE 441743 B SE441743 B SE 441743B SE 8204658 A SE8204658 A SE 8204658A SE 8204658 A SE8204658 A SE 8204658A SE 441743 B SE441743 B SE 441743B
- Authority
- SE
- Sweden
- Prior art keywords
- dihydropyridine
- nitrophenyl
- dimethyl
- dicarbometoxy
- preparing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 4
- -1 dimethyl-2,5-dicarbomethoxy-1,4-dihydropyridine Chemical compound 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LCJDFVKGOZCWJF-UHFFFAOYSA-N acetic acid;2-nitrobenzaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=CC=C1C=O LCJDFVKGOZCWJF-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
Description
8204658-2 10 15 20 25 30 2 av denna syntes är omkring 60 % av det teoretiska.
I förfarandet enligt uppfinningen användes ett visst reagens, d.v.s. 2-nitrobensaldehyddiacetat av formel II, för första gången vid syntes av 4-(2'-nitrofenyl)-2,6-dimetyl- 3,S-dikarbmetoxi-1,H-dihydropyridin. Sålunda ersätts det dyra utgångsmaterialet2-nitrobensaldehyd med det billigare 2-nitro- bensaldehyddiacetatet, vilket kan framställas på ovan beskrivet sätt. Föreningen omsätts med metylacetoacetat och ammoniak i närvaro av ett inert organiskt lösningsmedel, såsom metanol, och i närvaro eller frånvaro av en organisk bas, såsom pyridin, vid en temperatur mellan 20 och 150°C. Denna process, där ett syntessteg kan utelämnas - eftersom det inte finns behov av preliminär hydrolys av 2-nitrobensaldehyddiacetat av formel II till motsvarande 2-nitrobensaldehyd-, representerar en ny och förenklad Hantzsch-metod för syntes av pyridiner.
Uppfinningen àskàdliggöres av följande exempel- Exempel 1 2-nitrobensaldehyddiacetat (0,1 mol, 25,4 g), metyl- acetoacetat (0,2 mol, 23,2 g) och NH“0H (12 ml) värmdes i metanol (20 ml) i närvaro av pyridin under flera (7) timmar.
Efter kylning till 15°C avfiltrerades den utfällda produkten.
Râprodukten kristallíserades ur ättíksyra till 4-(2'-nitro- fenyl)-2,6-dimetyl-3,5-dikarbmetoxi-1,k-dihydropyridin (21,7 g, 82 % av teorin), smp. 172°-174°C.
Exempel 2 2-nitrobensaldehyddiacetat (0,1 mol, 25,H g), metyl- acetoacetat (0,21 mol, 26 g), NHuOH (12 ml) och metanol (M5 ml) värmdes under 5 timmar med àterlopp. Kristallisering av rå- produkten ur ättiksyra gav 4-(2'-nitrofenyl)-2,6-dimetyl-3,5- dikarbmetoxi-1,H-dihydropyridin (19,0 g, 55 % av teorin), smp. 173 - 17u°c.
Claims (1)
1. 820465 PATENTKRAV Förfarande för framställning av H-(2'-nítrofenyl)-2,& dimetyl-2,5-dikarbmetoxi-1,4-dihydropyridin av formeln NO Hacoo ß Cålfla CH3 t\g CH3 k ä n n e t e c k n a t av att 2-nitrobensaldehyddíacetat, metylacetoacetat och ammoniak omsätts i närvaro av ett inert organiskt lösningsmedel, såsom metanol, och i närvaro eller f varo av en organisk bas, såsom pyridin, vid en temperatur av mellan zo och 1so°c.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU2005/81A YU41983B (en) | 1981-08-19 | 1981-08-19 | Process for preparing 1,4-dihydro-pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8204658D0 SE8204658D0 (sv) | 1982-08-11 |
| SE8204658L SE8204658L (sv) | 1983-02-20 |
| SE441743B true SE441743B (sv) | 1985-11-04 |
Family
ID=25556467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8204658A SE441743B (sv) | 1981-08-19 | 1982-08-11 | Forfarande for framstellning av 4-(2?721-nitrofenyl)-2,6-dimetyl-3,5-dikarbometoxi-1,4-dihydropyridin |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4467093A (sv) |
| JP (1) | JPS5839663A (sv) |
| AT (1) | AT380876B (sv) |
| CA (1) | CA1185243A (sv) |
| CH (1) | CH651297A5 (sv) |
| DK (1) | DK155734C (sv) |
| ES (1) | ES8306364A1 (sv) |
| FI (1) | FI74275C (sv) |
| NL (1) | NL8203260A (sv) |
| PL (1) | PL131222B1 (sv) |
| SE (1) | SE441743B (sv) |
| SU (1) | SU1099842A3 (sv) |
| YU (1) | YU41983B (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
| JPH02118009U (sv) * | 1989-03-09 | 1990-09-21 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE2808930A1 (de) * | 1978-03-02 | 1979-09-06 | Bayer Ag | Verfahren zur herstellung von 2-nitrobenzaldehyd |
| JPS554318A (en) * | 1978-06-23 | 1980-01-12 | Asahi Chem Ind Co Ltd | Preparation of 1,4-dihydropyridine |
| JPS5520719A (en) * | 1978-07-31 | 1980-02-14 | Asahi Chem Ind Co Ltd | Preparation of 1,4-dihydropyridine derivative |
| JPS55124760A (en) * | 1979-03-16 | 1980-09-26 | Kanebo Ltd | Preparation of 1,4-dihydropyridine derivative or its salt |
-
1981
- 1981-08-19 YU YU2005/81A patent/YU41983B/xx unknown
-
1982
- 1982-07-27 US US06/402,487 patent/US4467093A/en not_active Expired - Fee Related
- 1982-07-29 CA CA000408333A patent/CA1185243A/en not_active Expired
- 1982-08-11 SE SE8204658A patent/SE441743B/sv not_active IP Right Cessation
- 1982-08-11 AT AT0307082A patent/AT380876B/de not_active IP Right Cessation
- 1982-08-16 FI FI822842A patent/FI74275C/sv not_active IP Right Cessation
- 1982-08-17 ES ES515063A patent/ES8306364A1/es not_active Expired
- 1982-08-17 CH CH4929/82A patent/CH651297A5/de not_active IP Right Cessation
- 1982-08-17 PL PL1982237935A patent/PL131222B1/pl unknown
- 1982-08-18 SU SU823482656A patent/SU1099842A3/ru active
- 1982-08-18 DK DK370382A patent/DK155734C/da not_active IP Right Cessation
- 1982-08-19 NL NL8203260A patent/NL8203260A/nl not_active Application Discontinuation
- 1982-08-19 JP JP57142768A patent/JPS5839663A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1185243A (en) | 1985-04-09 |
| DK155734C (da) | 1989-09-25 |
| FI822842A0 (fi) | 1982-08-16 |
| ES515063A0 (es) | 1983-06-01 |
| SU1099842A3 (ru) | 1984-06-23 |
| PL237935A1 (en) | 1983-02-28 |
| FI74275C (sv) | 1988-01-11 |
| PL131222B1 (en) | 1984-10-31 |
| SE8204658D0 (sv) | 1982-08-11 |
| SE8204658L (sv) | 1983-02-20 |
| JPS5839663A (ja) | 1983-03-08 |
| DK155734B (da) | 1989-05-08 |
| CH651297A5 (de) | 1985-09-13 |
| ATA307082A (de) | 1985-12-15 |
| US4467093A (en) | 1984-08-21 |
| YU200581A (en) | 1984-02-29 |
| ES8306364A1 (es) | 1983-06-01 |
| NL8203260A (nl) | 1983-03-16 |
| FI74275B (fi) | 1987-09-30 |
| YU41983B (en) | 1988-04-30 |
| JPS6314709B2 (sv) | 1988-04-01 |
| AT380876B (de) | 1986-07-25 |
| FI822842L (fi) | 1983-02-20 |
| DK370382A (da) | 1983-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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