FR2377384A1 - NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINS - Google Patents
NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINSInfo
- Publication number
- FR2377384A1 FR2377384A1 FR7800960A FR7800960A FR2377384A1 FR 2377384 A1 FR2377384 A1 FR 2377384A1 FR 7800960 A FR7800960 A FR 7800960A FR 7800960 A FR7800960 A FR 7800960A FR 2377384 A1 FR2377384 A1 FR 2377384A1
- Authority
- FR
- France
- Prior art keywords
- amino
- preparation
- hydroxyquinolines
- cyano
- hydroxyquinoleins
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical compound NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 title 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title 1
- LWGUCIXHBVVATR-UHFFFAOYSA-N 2-amino-1h-quinolin-4-one Chemical class C1=CC=C2NC(N)=CC(=O)C2=C1 LWGUCIXHBVVATR-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- ZCTNWWKUJWVBLJ-UHFFFAOYSA-N 2-amino-2-benzoylpropanedinitrile Chemical class N#CC(N)(C#N)C(=O)C1=CC=CC=C1 ZCTNWWKUJWVBLJ-UHFFFAOYSA-N 0.000 abstract 1
- USKBIWBLJHCVOP-UHFFFAOYSA-N 2-amino-4-oxo-1h-quinoline-3-carbonitrile Chemical class C1=CC=C2C(O)=C(C#N)C(N)=NC2=C1 USKBIWBLJHCVOP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne la préparation de 2-amino-4-hydroxyquinoléines. Le procédé consiste à faire réagir des anhydrides isatoïques avec le malononitrile dans un solvant inerte en présence d'une base pour produire des 2-amino-3-cyano-4-hydroxyquinoléines et des 2-amino- alpha , alpha -dicyanoacétophénones qui sont ensuite hydrolysées et décarboxylées dans des conditions acides ou basiques pour produire des 2-amino-4-hydroxyquinoléines. Les 2-amino-4-hydroxyquinoléines obtenues par le procédé de l'invention sont des composés intermédiaires pour la préparation d'acides 1-oxo- 1H-6-alkoxypyrimidoØl,2-alquinoleine-2- carboxyliques et de leurs esters, qui sont doués de propriétés anti-allergiques.The invention relates to the preparation of 2-amino-4-hydroxyquinolines. The process involves reacting isatoid anhydrides with malononitrile in an inert solvent in the presence of a base to produce 2-amino-3-cyano-4-hydroxyquinolines and 2-amino-alpha, alpha-dicyanoacetophenones which are then hydrolyzed and decarboxylated under acidic or basic conditions to produce 2-amino-4-hydroxyquinolines. The 2-amino-4-hydroxyquinolines obtained by the process of the invention are intermediate compounds for the preparation of 1-oxo-1H-6-alkoxypyrimidoØl, 2-alquinoleine-2-carboxylic acids and their esters, which are endowed with anti-allergic properties.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75929577A | 1977-01-14 | 1977-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2377384A1 true FR2377384A1 (en) | 1978-08-11 |
| FR2377384B1 FR2377384B1 (en) | 1982-08-06 |
Family
ID=25055125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7800960A Granted FR2377384A1 (en) | 1977-01-14 | 1978-01-13 | NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINS |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5390271A (en) |
| BE (1) | BE862883A (en) |
| DE (1) | DE2801248C3 (en) |
| DK (1) | DK15478A (en) |
| FR (1) | FR2377384A1 (en) |
| GB (1) | GB1567875A (en) |
| IE (1) | IE46298B1 (en) |
| IT (1) | IT1091846B (en) |
| LU (1) | LU78866A1 (en) |
| NL (1) | NL7800433A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019014402A1 (en) | 2017-07-14 | 2019-01-17 | Innate Tumor Immunity, Inc. | Nlrp3 modulators |
-
1978
- 1978-01-09 JP JP106178A patent/JPS5390271A/en active Granted
- 1978-01-12 DE DE2801248A patent/DE2801248C3/en not_active Expired
- 1978-01-12 DK DK15478A patent/DK15478A/en not_active Application Discontinuation
- 1978-01-13 IE IE71/78A patent/IE46298B1/en unknown
- 1978-01-13 GB GB1505/78A patent/GB1567875A/en not_active Expired
- 1978-01-13 FR FR7800960A patent/FR2377384A1/en active Granted
- 1978-01-13 NL NL7800433A patent/NL7800433A/en active Search and Examination
- 1978-01-13 IT IT19261/78A patent/IT1091846B/en active
- 1978-01-13 BE BE184295A patent/BE862883A/en not_active IP Right Cessation
- 1978-01-13 LU LU78866A patent/LU78866A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2801248B2 (en) | 1979-03-15 |
| JPS5625231B2 (en) | 1981-06-11 |
| JPS5390271A (en) | 1978-08-08 |
| FR2377384B1 (en) | 1982-08-06 |
| IT1091846B (en) | 1985-07-06 |
| DE2801248C3 (en) | 1979-10-31 |
| GB1567875A (en) | 1980-05-21 |
| NL7800433A (en) | 1978-07-18 |
| DE2801248A1 (en) | 1978-07-20 |
| IE46298B1 (en) | 1983-04-20 |
| LU78866A1 (en) | 1979-09-06 |
| DK15478A (en) | 1978-07-15 |
| BE862883A (en) | 1978-07-13 |
| IT7819261A0 (en) | 1978-01-13 |
| IE780071L (en) | 1978-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |