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Methyl iodide → 3-Bromo-5-ethyl-6-methoxy-2-methylpyridine

HRID 1921307
Notes
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Reaction equation

HRID 1921307 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH3:11])[C:5](=[O:9])[NH:6][C:7]=1[CH3:8].IC.Cl[CH2:15]Cl>[Al].C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH3:15])=[C:4]([CH2:10][CH3:11])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 6344DichloromethaneHCID 207792745-bromo-3-ethyl-6-methyl-1H-pyridin-2-one

Product 1

HCID 116586693-Bromo-5-ethyl-6-methoxy-2-methylpyridineYield 99.9%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalyst
HCID 5359268
Aluminum
Solvent

Procedure

A mixture of 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one (41.8 g, 0.193 mol) obtained from Step 2 as described above, iodomethane (70 mL, 1.12 mol), silver carbonate (72 g, 0.261 mol) and dichloromethane is mechanically stirred at ambient temperature for 17 hr (The reaction vessel is wrapped in aluminum foil). An additional portion of iodomethane (70 mL, 1.12 mol) is added and stirring continued for an additional 20 hr. The reaction mixture is filtered through a pad of Celite and the filter cake is washed with dichloromethane. The combined filtrate and wash is concentrated to afford the title compound (44.35 g, 99.9% yield) as a yellow oil.

Workup

  1. stirringstirring
  2. waitcontinued for an additional 20 hr
  3. filtrationThe reaction mixture is filtered through a pad of Celite
  4. washthe filter cake is washed with dichloromethane
  5. washThe combined filtrate and wash
  6. concentrationis concentrated

Sources & evidence

ORD record
ord-79397737d65c4134aa19e45d8cb77e6c
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173682B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes