Pyridine → Diethyl 2-(methoxyimino)malonate

HRID 1955589

Reaktionsgleichung

Reaktionsgleichung von HRID 1955589
O=[C:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:13][O:14][NH3+:15].[Cl-].N1C=CC=CC=1>C(O)C>[CH3:13][O:14][N:15]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 11639O-methylhydroxylammonium chlorideHCID 691051,3-Diethyl 2-oxopropanedioate

Produkt 1

HCID 533643Diethyl 2-(methoxyimino)malonateAusbeute 93.221,797 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of diethyl ketomalonate 1 (51.0 g, 0.293 mmol), o-methylhydroxylamine hydrochloride (24.46 g, 0.293 mmol) and pyridine (23.2 g, 0.293 mmol) in ethanol (250 ml) is heated to reflux for 3 hr. The solvent is removed under reduced pressure. The residue is dissolved in ethyl acetate and washed with water, dilute hydrogen chloride, aqueous sodium hydrogencarbonate solution, and water successively. After drying over sodium sulfate, the solvent is removed under reduced pressure. The resultant residue is distilled under reduced pressure at 80°-85° C./0.5 mmHg to obtain Compound 2 (55.5 g, 93.2%). NNMR (CDCl3)δ: 1.35 (3H, t, J=7.1 Hz), 1.35 (3H, t, J=7.1 Hz), 4.11 (3H, s), 4.36 (2H, q, J=7.1 Hz), 4.37 (2H, q, J=7.1 Hz).

Aufarbeitung

  1. temperatureto reflux for 3 hr
  2. customThe solvent is removed under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water, dilute hydrogen chloride, aqueous sodium hydrogencarbonate solution, and water successively
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. distillationThe resultant residue is distilled under reduced pressure at 80°-85° C./0.5 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-9d8b430b46584b7db1376447e5d64f17
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05776929

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