1,1,1-Trifluoro-2,4-pentanedione → HCID 178426050, Verbindung

HRID 482000

Reaktionsgleichung

Reaktionsgleichung von HRID 482000
NC1C(=O)NC=CC=1C(F)(F)F.[F:13][C:14]([F:22])([F:21])[C:15](=O)[CH2:16][C:17](=O)[CH3:18].[N+:23]([CH2:26][C:27]([NH2:29])=[O:28])([O-:25])=[O:24]>C(NCC)C>[OH:28][C:27]1[C:26]([N+:23]([O-:25])=[O:24])=[C:15]([C:14]([F:22])([F:21])[F:13])[CH:16]=[C:17]([CH3:18])[N:29]=1

Komponenten

5

Edukt 3

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 2792562-NitroacetamideHCID 19065070HCID 19065070, Verbindung

Produkt 1

HCID 178426050HCID 178426050, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A method for preparing compounds which are derivatives of 3-amino-4-trifluoromethyl-2-pyridinone is illustrated in Scheme 3. In Step A, 1,1,1, trifluoro-2,4-pentanedione is condensed with nitroacetamide in ethanolic diethylamine to give 2-hydroxy-6-methyl-3-nitro-4-trifluoromethylpyridine. This is alkylated in Step B with an acetate equivalent such as t-butyl bromoacetate in THF using sodium hydride as a base and the nitro group is reduced in Step C by hydrogenation using a catalyst such as palladium on carbon. The t-butyl group is removed in Step D by a strong acid such as HCl and the resulting carboxylic acid is coupled to ethyl-2-aminomethyl-4-chlorophenoxyacetamide in Step E to give the final product.

Aufarbeitung

  1. customA method for preparing compounds which

Quellen und Nachweise

ORD-Eintrag
ord-f8938fb8cd8f4acfb0e759b992727673
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792779

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