Dimethyl malonate → HCID 2764544, Verbindung

HRID 331550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331550
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:18][CH3:19])(=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[H-].[Na+]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:12]([C:11]([O:18][CH3:19])=[O:17])[C:13]([O:15][CH3:16])=[O:14])=[N:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydride2×HCID 783082-Chloro-5-nitropyridine

Produkt 1

HCID 2764544HCID 2764544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2-chloro-5-nitropyridine (25.0 g, 158 mmol) and dimethyl malonate (21.9 g, 166 mmol) in DMF (150 mL) was cooled to 0° C., and sodium hydride (6.50 g of a 60% dispersion in mineral oil, 162 mmol) was added in small portions. The mixture was stirred at 0° C. for 1 hour following completion of the addition. Then, another equivalent of sodium hydride (6.5 g of a 60% dispersion in mineral oil, 162 mmol) was added in small portions. The reaction was quenched by the addition of acetic acid (10 mL), and the mixture was evaporated to dryness. The residue was triturated with diethyl ether (150 mL) overnight and filtered, providing crude dimethyl 2-(5-nitropyridin-2-yl)malonate as an orange solid.

Aufarbeitung

  1. additioncompletion of the addition
  2. customThe reaction was quenched by the addition of acetic acid (10 mL)
  3. customthe mixture was evaporated to dryness
  4. customThe residue was triturated with diethyl ether (150 mL) overnight
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-2c86cb47d2f9404c91bceafed73f58ae
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877780B2

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