Methyl iodide → Methyl 6-cyanopyridine-3-carboxylate

HRID 1858015Notes

Reaction equation

HRID 1858015 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[C:9]([C:11]1[N:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1)#[N:10]>CC(C)=O>[C:9]([C:11]1[N:16]=[CH:15][C:14]([C:17]([O:19][CH3:1])=[O:18])=[CH:13][CH:12]=1)#[N:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27611086-Cyanopyridine-3-carboxylic acid

Product 1

HCID 13144281Methyl 6-cyanopyridine-3-carboxylateYield 80.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (6.1 g, 43.9 mmol) and methyl iodide (21 mL, 338 mmol) were added sequentially to a solution comprising 6-cyanopyridine-3-carboxylic acid (5 g, 33.8 mmol) in acetone (300 mL). The mixture was heated at reflux for 15 hours and concentrated under reduced pressure. The residue was partioned between ether and saturated sodium bicarbonate. The organic layer was washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to provide methyl 6-cyanopyridine-3-carboxylate (4.4 g, 27.1 mmol) as a tan solid. 1H-NMR (300 Mhz, DMSO-d6): 3.9 (s, 3H), 8.2 (d, 1H, J=7.5 Hz), 8.5 (d, 1H, J=7.5 Hz), 9.2 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 hours
  3. concentrationconcentrated under reduced pressure
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4908a2e7ef8b408484cc5abdebd3f604
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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