RU2002123358A - Способ получения 5-арилникотинальдегидов - Google Patents

Способ получения 5-арилникотинальдегидов

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RU2002123358A
RU2002123358A RU2002123358/04A RU2002123358A RU2002123358A RU 2002123358 A RU2002123358 A RU 2002123358A RU 2002123358/04 A RU2002123358/04 A RU 2002123358/04A RU 2002123358 A RU2002123358 A RU 2002123358A RU 2002123358 A RU2002123358 A RU 2002123358A
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Андреас БАТ (DE)
Андреас БАТ
Хайнц БОКЕЛЬ (DE)
Хайнц БОКЕЛЬ
Томас КАЙЛЬ (DE)
Томас КАЙЛЬ
Ральф КНИРИМЕН (DE)
Ральф КНИРИМЕН
Кристоф МЮРМАНН (DE)
Кристоф МЮРМАНН
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Мерк Патент ГмбХ (DE)
Мерк Патент Гмбх
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    • C07D213/60—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 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
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    • 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
    • C07D213/60—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 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
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    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
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    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Claims (7)

1. Изобретение относится к способу получения 5-арилникотинальдегидов восстановлением соответствующих 5-арилникотиновых кислот каталитической гидрогенизацией в присутствии карбоксильных ангидридов, в которой применяемый катализатор представляет собой палладиево-лигандный комплекс, отличающемуся тем, что молярное отношение между палладием и лигандом составляет от 1:5 до 1:15 в случае монозубых лигандов и от 1:2,5 до 1:7,5 в случае двузубых лигандов.
2. Способ получения 5-арилникотинальдегидов формулы I
Figure 00000001
в которой А обозначает фенильный радикал или нафтильный радикал, каждый из которых может быть незамещенным или монозамещенным либо полизамещенным группами R, F, Cl, Br, I, -CN, -NO2, -CF3, -OCF3, -OCHF2, -OCF2CF3, -OCHFCF3 или -ОН и в котором, кроме того, одна или более группы СН могут быть замещены N;
R обозначает Н, алкильный радикал с неразветвленной или разветвленной цепочкой, содержащий от 1 до 15 атомов углерода, монозамещенный группой -CF3 или, по крайней мере, монозамещенный фтором, и где, кроме того, одна или более группы СН2 в этих радикалах могут быть, независимо друг от друга, замещены группами -S-,-O-,-O-СО-,-СО-O-или-СН=СН- таким образом, что гетероатомы не расположены непосредственно рядом друг с другом, восстановлением соответствующих 5-арилникотиновых кислот каталитическим гидрированием в присутствии карбоновых ангидридов, в котором применяемый катализатор представляет собой палладиево-лигандный комплекс, отличающийся тем, что молярное отношение между палладием и лигандом составляет от 1:5 до 1:15 в случае монозубых лигандов и от 1:2,5 до 1:7,5 в случае двузубых лигандов.
3. Соединения формулы I, в которых А представляет собой 4-фторфенильную группу.
4. Соединения формул II, III, IV или V:
Figure 00000002
Figure 00000003
Figure 00000004
Figure 00000005
в которых А соответствует определению, приведенному в п.2, и R3 представляет собой метил, этил, n-пропил, изопропил, n-бутил, сек-бутил или трет-бутил.
5. Соединения формул II, III, IV или V, в которых А представляет собой 4-фторфенильную группу.
6. Применение соединения формулы I для получения N-алкилированных аминов.
7. Применение соединения формулы I для получения (R)-2-[5-(4-фторфенил)-3-пиридилметиламинометил]хромана.
RU2002123358/04A 2000-02-07 2001-01-05 Способ получения 5-(4-фторфенил)никотинальдегида соединения RU2256653C2 (ru)

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DE102004028561A1 (de) * 2004-06-15 2006-01-05 Merck Patent Gmbh Verfahren zur Herstellung von 5-Arylnicotinaldehyden
CN108997224B (zh) * 2018-08-28 2023-04-28 韶远科技（上海)有限公司 一种2-氯-5-氰基含氮六元杂环化合物的制备方法

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USRE41008E1 (en) 2009-11-24
NO20023702L (no) 2002-08-06
KR20020072241A (ko) 2002-09-14
PL205973B1 (pl) 2010-06-30
ES2350683T3 (es) 2011-01-26
WO2001058873A1 (de) 2001-08-16
CA2399125C (en) 2009-06-02
AU2001235395B2 (en) 2005-06-02
RU2256653C2 (ru) 2005-07-20
DE50115594D1 (de) 2010-09-23
DE10005150A1 (de) 2001-08-09
NO20023702D0 (no) 2002-08-06
CN1213031C (zh) 2005-08-03
AU3539501A (en) 2001-08-20
HUP0204436A2 (hu) 2003-08-28
CA2399125A1 (en) 2001-08-16
ATE477241T1 (de) 2010-08-15
CZ20022539A3 (cs) 2002-10-16
BR0108062A (pt) 2003-01-21
US20030055259A1 (en) 2003-03-20
US6703509B2 (en) 2004-03-09
CN1398256A (zh) 2003-02-19

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