Nicotinic Acid → N-Methoxy-N-methylnicotinamide

HRID 593507

Reaktionsgleichung

Reaktionsgleichung von HRID 593507
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:14][O:15][NH:16][CH3:17].C(N(CC)CC)C>>[CH3:17][N:16]([O:15][CH3:14])[C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 24386Thionyl Chloride

Produkt 1

HCID 10558996N-Methoxy-N-methylnicotinamide

Versuchsvorschrift

A flask is charged with nicotinic acid (5.0 g, 40.6 mmol). Thionyl chloride (30.0 mL) is added and the reaction is refluxed for 1 h. It is then cooled to room temperature and concentrated in vacuo. The residue is dissolved in anhydrous dichloromethane (30 mL) and O,N-dimethyl-hydroxylamine (4.35 g, 44.0 mmol) is added, followed by addition of triethylamine (14.15 g, 100.0 mmol). The reaction mixture is stirred at room temperature for 1.5 h. It is then washed with water and the aqueous phase is extracted with dichloromethane. The combined organic layer is dried over sodium sulfate and concentrated in vacuo to afford N-methyl-N-methoxy-nicotinamide as a brown oil. MS (ESI) m/z 167.0 (M+H)+.

Aufarbeitung

  1. temperaturethe reaction is refluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in anhydrous dichloromethane (30 mL)
  4. washIt is then washed with water
  5. extractionthe aqueous phase is extracted with dichloromethane
  6. dry with materialThe combined organic layer is dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cdf6e6329b7044669a3248a1d08e0744
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242963B2

Verknüpfte Notizen

Wird geladen…