Methyl iodide → 2-Iodo-3-methoxy-6-methylpyridine

HRID 1632061

Reaction equation

HRID 1632061 reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[I:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 899572-Iodo-6-methylpyridin-3-ol

Product 1

HCID 114820512-Iodo-3-methoxy-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To 2-iodo-6-methyl-pyridin-3-ol (1.0 g, 4.25 mmol) and K2CO3 (1.18 g, 8.51 mmol) in acetone (20 mL) was added MeI (0.91 g, 6.38 mmol). The reaction was stirred at 45° C. under N2 for 20 h. The reaction was cooled to room temperature and concentrated. The residue was purified by silica gel column chromatography using dichloromethane to afford 1.04 g (98%) of I-95 as light yellow solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography
  4. customto afford 1.04 g (98%) of I-95 as light yellow solid

Sources & evidence

ORD record
ord-d1047a62b074498984bbe748110cc45d
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Linked notes

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