4-Methylmorpholine → 6-Chloro-nicotinic Acid N'-(2-ethoxy-acetyl)-hydrazide

HRID 254252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254252
[CH3:1][CH2:2][O:3][CH2:4][C:5](Cl)=[O:6].[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][N:10]=1.CN1CCOCC1>ClCCl>[CH2:2]([O:3][CH2:4][C:5]([NH:16][NH:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][C:9]([Cl:8])=[N:10][CH:11]=1)=[O:6])[CH3:1]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 84189Ethoxyacetyl chlorideHCID 28001776-Chloropyridine-3-carbohydrazide

Produkt 1

HCID 589974826-Chloro-nicotinic Acid N'-(2-ethoxy-acetyl)-hydrazideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(2-Ethoxy)-acetyl chloride [(1.72 g, 13.99 mmol), Tett. Lett., 35, (39), 7269; 1994)] was added to an ice-cold solution of 6-chloronicotinic acid hydrazide (2 g, 11.66 mmol) and N-methylmorpholine (1.92 mL, 17.49 mmol) in dichloromethane (60 mL) and the mixture was stirred at room temperature for 18 hours. The mixture was then washed with citric acid, sodium hydrogen carbonate solution and brine and the solvent was evaporated under reduced pressure to yield some title product as a white solid, 880 mg. The combined aqueous washings were extracted with ethyl acetate (×2) and the combined organic solutions were dried over sodium sulfate and concentrated in vacuo to afford a further crop of title compound as a pale yellow solid, 1.6 g (total yield of 83%).

Aufarbeitung

  1. washThe mixture was then washed with citric acid, sodium hydrogen carbonate solution and brine
  2. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a98d691c4edc4a7ea0579b35d0db799e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875615B2

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