Trimethylsilyldiazomethane → Methyl 2-acetamidoisonicotinate

HRID 1740946

Reaktionsgleichung

Reaktionsgleichung von HRID 1740946
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=1)([OH:3])=[O:2].[Si](C=[N+]=[N-])(C)(C)[CH3:15]>CO.C1C=CC=CC=1>[CH3:15][O:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=1)=[O:3]

Komponenten

4

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 37744662-Acetamidopyridine-4-carboxylic acid

Produkt 1

HCID 22185175Methyl 2-acetamidoisonicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21927730Benzene methanolLösungsmittel

Versuchsvorschrift

4-Carboxy-2-acetylaminopyridine (3.4 g, 19 mmol) was dissolved in methanol/benzene (100 mL, 1:1). TMS-diazomethane was added (1M, Aldrich) with cooling until the yellow color just persisted, then the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (50/50 hexane/ethyl acetate) and 3.0 g of product was recovered.

Aufarbeitung

  1. temperaturewith cooling until the yellow color
  2. customthe solvent was removed under reduced pressure
  3. customThe product was purified by silica gel column chromatography (50/50 hexane/ethyl acetate) and 3.0 g of product
  4. customwas recovered

Quellen und Nachweise

ORD-Eintrag
ord-5841a4b889fc4ec4832020a9bd18915c
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972975

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