Sarcosine methyl ester → Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinate

HRID 716268

Reaktionsgleichung

Reaktionsgleichung von HRID 716268
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:15][NH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>ClCCl>[CH3:21][O:20][C:18](=[O:19])[CH2:17][N:16]([CH3:15])[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 83545Sarcosine methyl esterHCID 346961Methyl 6-chloro-5-nitronicotinate

Produkt 1

HCID 58324470Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinateAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(methylamino)acetate (1.9 g, 18.47 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one hour and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified using flash column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes) to yield 2.60 g (99% yield) of the title compound as a yellow oil. [M+H] calc'd for C11H13N3O6, 284. found, 284.

Aufarbeitung

  1. customThe viscous yellow reaction
  2. temperaturewas heated to 90° C. for one hour
  3. temperatureto cool back to room temperature
  4. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-e35c11cc9ed94991931c21d08f8e53a9
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187497B2

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