1,1'-Carbonyldiimidazole → 2-Methylnicotinamide

HRID 52364Notes

Reaction equation

HRID 52364 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N1C=CN=C1)([N:13]1C=CN=C1)=O>C(Cl)Cl>[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:13])=[O:5]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 6433732-Methylnicotinic acid

Product 1

HCID 122437052-MethylnicotinamideYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-methylnicotinic acid (15.0 g, 0.111 mol) and 1,1'-carbonyldiimidazole (36.0 g, 0.222 mol) was added 300 mL of methylene chloride dropwise. The reaction mixture was stirred at room temperature overnight. Ammonia gas was distilled into the reaction mixture for 30 minutes using a dry ice condenser and the mixture was stirred at room temperature for an additional hour. Solvent was removed under vacuum and the residue was dissolved with 500 mL of acetonitrile. The solution was concentrated to half volume at low temperature and the product precipitated out as white solid. The crude mixture was recrystallized from ethanol/ether to give 11.5 g of 2-methylnicotinamide as a colorless crystal (76%): mp 160°-163° C. Anal. Calc'd. For C7H8N2O: C, 61.75, H, 5.92, N, 20.57. Found: C, 61.44, H, 6.14, N, 20.66.

Workup

  1. distillationAmmonia gas was distilled into the reaction mixture for 30 minutes
  2. stirringthe mixture was stirred at room temperature for an additional hour
  3. customSolvent was removed under vacuum
  4. dissolutionthe residue was dissolved with 500 mL of acetonitrile
  5. concentrationThe solution was concentrated to half volume at low temperature
  6. customthe product precipitated out as white solid
  7. customThe crude mixture was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-9ade0c7d66594163bb990bd6e6480ebc
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

Loading…