Ammonia → 5-Cyano-3-methyl-2-pyridinecarboxamide

HRID 2196359Notes

Reaction equation

HRID 2196359 reaction equation
C[O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]#[N:13])=[CH:7][N:6]=1)=O.[NH3:14]>CO>[C:12]([C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]([NH2:14])=[O:2])=[N:6][CH:7]=1)#[N:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66665483Methyl 5-cyano-3-methylpyridine-2-carboxylate

Product 1

HCID 666659355-Cyano-3-methyl-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-cyano-3-methylpyridine-2-carboxylic acid methyl ester (1 g, 5.6 mmol) in methanol (5 mL) was added ammonia (4 mL, 28 mmol, 7N solution in methanol). The mixture was then heated at 50° C. with stirring in a sealed tube. After 60 min, HPLC analysis revealed completion of reaction. The mixture was concentrated in vacuo to give the title compound as a pale yellow solid: ESIMS: 162; [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.87 (d, 1H), 8.30 (d, 1H), 8.09 (br s, 1H), 7.74 (br s, 1H), 2.50 (s, 3H)

Workup

  1. customcompletion of reaction
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d5e679bd0d6c40fb99ea25d486efdcc4
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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