Acetic Anhydride → 6-Acetamidopyridine-3-carboxamide

HRID 127943Notes

Reaction equation

HRID 127943 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>CS(C)=O>[C:11]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 95006-Aminonicotinamide

Product 1

HCID 2529266-Acetamidopyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Amino nicotinamide 13.7 g (0.1 mole) is dissolved in 100 ml of dimethylsulfoxide and acetic anhydride 14.2 ml (0.15 mole) is added to the above solution. The mixture is stirred at room temperature for 16 hours. White crystals which are formed during the reaction are isolated by filtration and are purified by washing with 0.2 N HCl and ethanol. 6-Acetylamino nicotinamide 9.5 g thus synthesized is practically pure as shown by infrared spectroscopy and thin-layer chromatography.

Workup

  1. customWhite crystals which are formed during the reaction
  2. customare isolated by filtration
  3. customare purified
  4. washby washing with 0.2 N HCl and ethanol
  5. custom6-Acetylamino nicotinamide 9.5 g thus synthesized

Sources & evidence

ORD record
ord-3882579bd32c45989f054d56f505c570
Source dataset
uspto-grants-1981_03
Patent number
US04258052

Reaction notes

Loading…