HCID 178526432, Verbindung → HCID 66690045, Verbindung

HRID 505977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505977
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[C:8]3[CH2:12][C:11]([C:6]=2[CH:5]=1)=[CH:10][CH:9]=3)([O-])=O>[Ni].[Pd].CO>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[CH:8]3[CH2:12][CH:11]([C:6]=2[CH:5]=1)[CH2:10][CH2:9]3

Komponenten

5

Edukt 1

HCID 178526432HCID 178526432, Verbindung

Produkt 1

HCID 66690045HCID 66690045, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

In the synthesis shown in Scheme 1, a 3-nitrobenzene, generated from a 6-nitro-anthranilic acid (A), is reacted with a cyclic 1,4-diene (B), such as 5-isopropyl-cyclopentadiene, to form a 5-nitro-benzonorbornadiene (C) in a Diels-Alder reaction. Under standard catalytic reduction conditions (for example, using Raney nickel or palladium on carbon in a solvent such as methanol), both the 5-nitro group and the 2,3-double bond of the 5-nitro-benzonorbornadiene (C) are reduced to form the 5-amino-benzonorbornene (D). Reaction of the 5-amino-benzonorbornene (D) with a heterocyclyl-carboxylic acid or heterocyclyl-carboxylic acid derivative (E), where Q may be hydroxyl, fluoro, chloro or bromo, in a solvent such as dichloromethane gives a fungicidal heterocyclyl-carboxylic acid benzonorbornen-5-yl-amide (F). An example of (D) is 5-amino-9-isopropyl-benzonorbornene, which is a precursor of an amide of, for example, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid.

Aufarbeitung

  1. customin a Diels-Alder reaction

Quellen und Nachweise

ORD-Eintrag
ord-c2cd276fa13040e19f60541e92577d6f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781615B2

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