MX3019E - IMPROVED PROCEDURE TO PRODUCE PIRIMIDO - [4, 5 - b] QUINOLIN - 4 (3 H) - ON - 2 - ALKYL CARBOXYLATES - Google Patents
IMPROVED PROCEDURE TO PRODUCE PIRIMIDO - [4, 5 - b] QUINOLIN - 4 (3 H) - ON - 2 - ALKYL CARBOXYLATESInfo
- Publication number
- MX3019E MX3019E MX000113U MX11376U MX3019E MX 3019 E MX3019 E MX 3019E MX 000113 U MX000113 U MX 000113U MX 11376 U MX11376 U MX 11376U MX 3019 E MX3019 E MX 3019E
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- hydrogen
- sodium
- quinolin
- Prior art date
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La presente invención se refiere a un procedimiento mejorado para producir pirimido-[4,5-b] quinolin-4(3H)-on-2-carboxilatos de alquilo, caracterizado por hacer reaccionar un compuesto de 2-aminoquinolin-3-carboxamida que tiene la fórmula (VER FIGURA) en donde R1 es hidrógeno, alquilo que tiene de dos a cuatro átomos de carbono o fenilo; dos de los símbolos R2, R3, R4 y R5 son hidrógeno, alquilo que tiene de uno a cuatro átomos de carbono, alcoxi que tiene de uno a cuatro átomos de carbono, halo, benciloxi, metiltio o benciltio y el resto son hidrógeno, alquilo que tiene de uno a cuatro átomos de carbono, alcoxi que tiene de uno a cuatro átomos de carbono, o halo; R2 y R3, R3 y R4 cuando se toman juntas son alquilendioxi y son metilendioxi o etilendioxi, con de uno a tres equivalentes molares de oxalato de alquilo, en donde cada uno de los grupos alquilo tiene de uno a cuatro átomos de carbono, a una temperatura que va desde aproximadamente 20°C. hasta aproximadamente 100°C., en un solvente inerte a la reacción y en presencia de dos a tres equivalentes molares de una base por mol de 2-aminoquinolin-3-carboxamida y siendo dicha base alcóxido de sodio que tiene de uno a cuatro átomos de carbono, trifenilmetilsodio, hidruro de sodio, amida de sodio, 3-aminopropilamida de sodio o los compuestos de potasio correspondientes.The present invention relates to an improved process for producing alkyl pyrimido- [4,5-b] quinolin-4 (3H) -on-2-carboxylates, characterized by reacting a 2-aminoquinolin-3-carboxamide compound which it has the formula (SEE FIGURE) where R1 is hydrogen, alkyl having two to four carbon atoms or phenyl; two of the symbols R2, R3, R4 and R5 are hydrogen, alkyl having one to four carbon atoms, alkoxy having one to four carbon atoms, halo, benzyloxy, methylthio or benzylthio and the rest are hydrogen, alkyl having one to four carbon atoms, alkoxy having one to four carbon atoms, or halo; R2 and R3, R3 and R4 when taken together are alkylenedioxy and are methylenedioxy or ethylenedioxy, with from one to three molar equivalents of alkyl oxalate, where each of the alkyl groups has from one to four carbon atoms, to one temperature ranging from about 20 ° C. up to about 100 ° C., in a reaction inert solvent and in the presence of two to three molar equivalents of one base per mole of 2-aminoquinolin-3-carboxamide and said base being sodium alkoxide having from one to four atoms carbon, triphenylmethylsodium, sodium hydride, sodium amide, sodium 3-aminopropylamide or the corresponding potassium compounds.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57131875A | 1975-04-24 | 1975-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX3019E true MX3019E (en) | 1980-02-13 |
Family
ID=24283193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX000113U MX3019E (en) | 1975-04-24 | 1976-03-25 | IMPROVED PROCEDURE TO PRODUCE PIRIMIDO - [4, 5 - b] QUINOLIN - 4 (3 H) - ON - 2 - ALKYL CARBOXYLATES |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS51127098A (en) |
| AR (1) | AR207814A1 (en) |
| AT (1) | AT351549B (en) |
| BG (1) | BG27356A3 (en) |
| CA (1) | CA1065863A (en) |
| CH (1) | CH609056A5 (en) |
| DD (1) | DD125208A5 (en) |
| DK (1) | DK142323B (en) |
| ES (1) | ES446498A1 (en) |
| FI (1) | FI761020A (en) |
| HU (1) | HU172062B (en) |
| LU (1) | LU74787A1 (en) |
| MX (1) | MX3019E (en) |
| NL (1) | NL161155C (en) |
| PL (1) | PL101824B1 (en) |
| PT (1) | PT65023B (en) |
| RO (1) | RO68966A (en) |
| SE (1) | SE7603133L (en) |
| SU (1) | SU638261A3 (en) |
| YU (1) | YU79176A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5361243A (en) * | 1976-11-12 | 1978-06-01 | Fujitsu Ltd | 1-chip arithmetic circuit device |
| WO2004034985A2 (en) * | 2002-10-16 | 2004-04-29 | Smithkline Beecham Corporation | Chemical compounds |
-
1976
- 1976-01-01 AR AR262884A patent/AR207814A1/en active
- 1976-03-09 SE SE7603133A patent/SE7603133L/en unknown
- 1976-03-10 CA CA247,583A patent/CA1065863A/en not_active Expired
- 1976-03-25 MX MX000113U patent/MX3019E/en unknown
- 1976-03-26 YU YU00791/76A patent/YU79176A/en unknown
- 1976-03-30 ES ES446498A patent/ES446498A1/en not_active Expired
- 1976-03-30 DK DK143876AA patent/DK142323B/en not_active IP Right Cessation
- 1976-03-30 NL NL7603293.A patent/NL161155C/en active
- 1976-04-07 SU SU762343061A patent/SU638261A3/en active
- 1976-04-07 CH CH439876A patent/CH609056A5/en not_active IP Right Cessation
- 1976-04-13 JP JP51041749A patent/JPS51127098A/en active Granted
- 1976-04-13 AT AT270076A patent/AT351549B/en not_active IP Right Cessation
- 1976-04-13 BG BG032890A patent/BG27356A3/en unknown
- 1976-04-14 FI FI761020A patent/FI761020A/fi not_active Application Discontinuation
- 1976-04-15 DD DD192403A patent/DD125208A5/xx unknown
- 1976-04-16 LU LU74787A patent/LU74787A1/xx unknown
- 1976-04-16 HU HU76PI00000521A patent/HU172062B/en unknown
- 1976-04-17 PL PL1976188875A patent/PL101824B1/en unknown
- 1976-04-17 RO RO7685654A patent/RO68966A/en unknown
- 1976-04-19 PT PT65023A patent/PT65023B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL161155B (en) | 1979-08-15 |
| DK143876A (en) | 1976-10-25 |
| DK142323B (en) | 1980-10-13 |
| PT65023B (en) | 1977-09-09 |
| RO68966A (en) | 1981-05-30 |
| NL7603293A (en) | 1976-10-26 |
| SE7603133L (en) | 1976-10-25 |
| AT351549B (en) | 1979-07-25 |
| AR207814A1 (en) | 1976-10-29 |
| LU74787A1 (en) | 1977-02-07 |
| YU79176A (en) | 1982-05-31 |
| ATA270076A (en) | 1979-01-15 |
| SU638261A3 (en) | 1978-12-15 |
| NL161155C (en) | 1980-01-15 |
| ES446498A1 (en) | 1977-06-16 |
| CA1065863A (en) | 1979-11-06 |
| PT65023A (en) | 1976-05-01 |
| CH609056A5 (en) | 1979-02-15 |
| BG27356A3 (en) | 1979-10-12 |
| DD125208A5 (en) | 1977-04-06 |
| DK142323C (en) | 1981-06-29 |
| JPS543880B2 (en) | 1979-02-27 |
| PL101824B1 (en) | 1979-02-28 |
| JPS51127098A (en) | 1976-11-05 |
| HU172062B (en) | 1978-05-28 |
| FI761020A (en) | 1976-10-25 |
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