AR049397A1 - PROCEDURE FOR THE PREPARATION OF ALDEHIDS OF 5- ARYLNICOTINE BY CATALYTIC HYDROGENATION WITH A PALADIO COMPLEX - Google Patents
PROCEDURE FOR THE PREPARATION OF ALDEHIDS OF 5- ARYLNICOTINE BY CATALYTIC HYDROGENATION WITH A PALADIO COMPLEXInfo
- Publication number
- AR049397A1 AR049397A1 ARP050102443A ARP050102443A AR049397A1 AR 049397 A1 AR049397 A1 AR 049397A1 AR P050102443 A ARP050102443 A AR P050102443A AR P050102443 A ARP050102443 A AR P050102443A AR 049397 A1 AR049397 A1 AR 049397A1
- Authority
- AR
- Argentina
- Prior art keywords
- arylnicotinic
- arylnicotine
- butyldicarbonate
- varies
- preparation
- Prior art date
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title abstract 9
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000002253 acid Substances 0.000 abstract 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- 229910052763 palladium Inorganic materials 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/48—Aldehydo radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Es objeto de la presente un procedimiento para la preparacion de aldehídos de 5-arilnicotina por reduccion de los correspondientes ácidos 5-arilnicotínicos por medio de hidrogenacion catalítica con un complejo de paladio estabilizado con fosfina en presencia de diter.butildicarbonato, caracterizado porque la relacion molar de complejo de paladio a ácido 5-arilnicotínico varía entre 1:500 y 1:8000 y la relacion molar de ácido 5-arilnicotínico a di-ter.-butildicarbonato varía entre 1:1 y 1:5. Reivindicacion 4: Procedimiento para la preparacion de aldehídos de 5-arilnicotina de la formula (1), en donde A es un radical fenilo o un radical naftilo insustituido o mono- o polisustituido con R, F, Cl, -CN, -NO2, -CF3, -OCF3, -OCHF2, - OCF2CF3, OCHFCF3 u -Oalquilo, en donde también uno o varios grupos CF pueden estar reemplazados por N, y R es H, un radical alquilo de cadena lineal o ramificada, monosustituido con -CF3 o al menos monosustituido con fluor, con 1 a 15 átomos de C, en donde en estos radicales también uno o varios grupos CH2 también pueden estar reemplazados, de modo independiente entre sí, por -S-, -O-, -O-CO-, -CO-O- o -CH=CH-, de modo tal que los heteroátomos no son directamente adyacentes, por reduccion de los correspondientes ácidos 5-arilnicotínicos por medio de hidrogenacion catalítica con un complejo de paladio estabilizado con fosfina en presencia de di-ter.-butildicarbonato, caracterizado porque la relacion molar de complejo de paladio a ácido 5- arilnicotínico varía entre 1:5000 y 1:80000 y la relacion molar de ácido 5-arilnicotínico a di-ter.-butildicarbonato varía entre 1:1 y 1:5.A process for the preparation of 5-arylnicotine aldehydes by reduction of the corresponding 5-arylnicotinic acids by means of catalytic hydrogenation with a palladium complex stabilized with phosphine in the presence of diter.butyldicarbonate is characterized, characterized in that the molar ratio is Palladium complex to 5-arylnicotinic acid varies between 1: 500 and 1: 8000 and the molar ratio of 5-arylnicotinic acid to di-ter.-butyldicarbonate varies between 1: 1 and 1: 5. Claim 4: Process for the preparation of 5-arylnicotine aldehydes of the formula (1), wherein A is a phenyl radical or an unsubstituted or mono- or polysubstituted naphthyl radical with R, F, Cl, -CN, -NO2, -CF3, -OCF3, -OCHF2, - OCF2CF3, OCHFCF3 or -Oalkyl, where also one or more CF groups can be replaced by N, and R is H, a straight or branched chain alkyl radical, monosubstituted with -CF3 or at least one monosubstituted with fluorine, with 1 to 15 C atoms, where in these radicals also one or more CH2 groups can also be replaced, independently of each other, by -S-, -O-, -O-CO- , -CO-O- or -CH = CH-, so that the heteroatoms are not directly adjacent, by reduction of the corresponding 5-arylnicotinic acids by means of catalytic hydrogenation with a palladium complex stabilized with phosphine in the presence of di -ter.-butyldicarbonate, characterized in that the molar ratio of palladium complex to acid 5- arylnicotinic varies between 1: 5000 and 1: 80000 and the molar ratio of 5-arylnicotinic acid to di-ter.-butyldicarbonate varies between 1: 1 and 1: 5.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200410028561 DE102004028561A1 (en) | 2004-06-15 | 2004-06-15 | Process for the preparation of 5-arylnicotinaldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR049397A1 true AR049397A1 (en) | 2006-07-26 |
Family
ID=34967791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050102443A AR049397A1 (en) | 2004-06-15 | 2005-06-15 | PROCEDURE FOR THE PREPARATION OF ALDEHIDS OF 5- ARYLNICOTINE BY CATALYTIC HYDROGENATION WITH A PALADIO COMPLEX |
Country Status (3)
| Country | Link |
|---|---|
| AR (1) | AR049397A1 (en) |
| DE (1) | DE102004028561A1 (en) |
| WO (1) | WO2005123682A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006018843A1 (en) * | 2006-04-22 | 2007-10-25 | Lanxess Deutschland Gmbh | Stabilization of dicarbonic diesters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69926243T2 (en) * | 1998-08-27 | 2006-04-20 | Japan Science And Technology Agency, Kawaguchi | CATALYTIC PREPARATION OF ALDEHYDE BY DIRECT HYDROGENATION OF CARBOXYLIC ACIDS |
| DE10005150A1 (en) * | 2000-02-07 | 2001-08-09 | Merck Patent Gmbh | Process for the preparation of 5-arylnicotinaldehydes |
-
2004
- 2004-06-15 DE DE200410028561 patent/DE102004028561A1/en not_active Withdrawn
-
2005
- 2005-05-18 WO PCT/EP2005/005397 patent/WO2005123682A1/en not_active Ceased
- 2005-06-15 AR ARP050102443A patent/AR049397A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE102004028561A1 (en) | 2006-01-05 |
| WO2005123682A1 (en) | 2005-12-29 |
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