Trimethylsilyldiazomethane → Methyl 2-acetamidoisonicotinate

HRID 1740946Notes

Reaction equation

HRID 1740946 reaction equation
[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]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 37744662-Acetamidopyridine-4-carboxylic acid

Product 1

HCID 22185175Methyl 2-acetamidoisonicotinate

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5841a4b889fc4ec4832020a9bd18915c
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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