Methyl iodide → Methyl 2-(benzyloxy)isonicotinate

HRID 852066Notes

Reaction equation

HRID 852066 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](=O)([O-])O.[K+].IC>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([O:14][CH3:18])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 229262722-(Benzyloxy)pyridine-4-carboxylic acid

Product 1

HCID 22926252Methyl 2-(benzyloxy)isonicotinateYield 97.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(benzyloxy)isonicotinic acid (12.6 g) and potassium hydrogencarbonate (8.3 g) in N,N-dimethylformamide (180 mL) was added dropwise iodomethane (4.8 mL) under ice-cooling, and then stirred at room temperature for 7 hours. The reaction solution was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride (×3), and then dried over anhydrous sodium sulfate and concentrated to give the title compound as a brown oil (13.07 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated ammonium chloride (×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1fb28f39a8a44aeb437aa620db3eb4e
Source dataset
uspto-grants-2007_08
Patent number
US07253178B2

Reaction notes

Loading…