Hydrochloric Acid → 2-Chloro-N-methoxy-N-methylnicotinamide

HRID 419136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419136
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(=O)(O)[O-].[Na+].Cl.[CH3:17][NH:18][O:19][CH3:20].Cl>C1COCC1.O>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:18]([O:19][CH3:20])[CH3:17])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27745412-Chloronicotinoyl chloride

Produkt 1

HCID 102360762-Chloro-N-methoxy-N-methylnicotinamideAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-nicotinoyl chloride (7.00 g, 39.8 mmol) and sodium bicarbonate (10.0 g, 119 mmol) in 1:1 THF/H2O (110 mL) at 0° C. was added N,O-dimethyl hydroxylamine hydrochloride (4.68 g, 47.7 mmol). The resultant solution was stirred 2 h at 0° C., neutralized with 10% HCl to pH ˜7, and the aqueous layer was extracted two times with EtOAc. The combined organics were dried with sodium sulfate and concentrated in vacuo to produce 6.96 g (87%) of the crude nicotinamide, which was used without further purification.

Aufarbeitung

  1. extractionthe aqueous layer was extracted two times with EtOAc
  2. dry with materialThe combined organics were dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9a0fea562519448fa7ad61231dc35983
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093247B2

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