Sodium hydride → ethyl 4-{N-[3-(3-chlorobenzoyl)-6-methylpyridin-2-yl]-N-ethylcarbamoyl}butanoate

HRID 1582956

Reaktionsgleichung

Reaktionsgleichung von HRID 1582956
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:8]([NH:14][CH2:15][CH3:16])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:6].[H-].[Na+].Cl[CH:23]([CH2:29][CH2:30][C:31]([O-:33])=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:8]([N:14]([CH2:15][CH3:16])[C:31]([CH2:30][CH2:29][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:33])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 110549023-(3-Chlorobenzoyl)-2-ethylamino-6-methylpyridineHCID 22716689Monoethyl chloroglutarate

Produkt 1

HCID 22716702ethyl 4-{N-[3-(3-chlorobenzoyl)-6-methylpyridin-2-yl]-N-ethylcarbamoyl}butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A DMF solution of 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine was treated with 60% sodium hydride and then reacted with monoethyl chloroglutarate under heating. Thereafter, the whole was worked up and purified in a usual manner to obtain ethyl 4-{N-[3-(3-chlorobenzoyl)-6-methylpyridin-2-yl]-N-ethylcarbamoyl}butanoate. The resulting compound was reacted with sodium methoxide in ethanol under heating, then concentrated sulfuric acid was added to the reaction mixture, followed by reaction under heating for 2 days. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain ethyl 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate. MS: 399.

Aufarbeitung

  1. temperatureunder heating
  2. custompurified in a usual manner

Quellen und Nachweise

ORD-Eintrag
ord-275262b710cf4a448b90a8a6fff1385a
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740662B1

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