Methyl iodide → HCID 57975878, compound

HRID 1865648Notes

Reaction equation

HRID 1865648 reaction equation
[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[C:11]([O:12][CH3:14])=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57975900HCID 57975900, compound

Product 1

HCID 57975878HCID 57975878, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-pyridine-2-carboxylic acid methoxy-methyl-amide (5.21 g, 28.60 mmol), N,N-dimethylformamide (500 ml), potassium carbonate (15.91 g), and methyl iodide (3.6 ml, 57.70 mmol) were stirred for 18 hours at room temperature. The reaction was concentrated. Water and ethyl acetate was added. The organic layer was separated, dried over sodium sulfate, and concentrated. The crude material was purified by flash chromatography (0-70% [10% methanol in ethyl acetate] in hexanes) to give 1.58 g (28%) of 3-methoxy-pyridine-2-carboxylic acid methoxy-methyl-amide. 1H NMR (250 MHz, CDCl3) δ 8.20-8.11 (m, 1H), 7.32-7.18 (m, 2H), 3.83 (s, 3H), 3.51 (s, 3H), 3.35 (s, 3H); MS: m/z 310.6+197.1 (M+H+).

Workup

  1. concentrationThe reaction was concentrated
  2. additionWater and ethyl acetate was added
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (0-70% [10% methanol in ethyl acetate] in hexanes)

Sources & evidence

ORD record
ord-25916226113943dfa7737552ab58158c
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

Loading…