HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 249736
Notes
Print preview

Reaction equation

HRID 249736 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].[CH3:12]I>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH3:12])=[C:4]([CH2:10][CH3:11])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 207792745-bromo-3-ethyl-6-methyl-1H-pyridin-2-one

Product 1

HCID 116586693-Bromo-5-ethyl-6-methoxy-2-methylpyridineYield 6,287.1%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

5-Bromo-3-ethyl-6-methyl-1H-pyridin-2-one (25 g, 115.7 mmol) was dissolved in 200 ml of chloroform to form an orange solution. Silver carbonate (31.9 g, 115.7 mmol) was added and the mixture was vigorously stirred. Methyl iodide (10.8 ml, 1.5 mmol) was added to this suspension, which was then stirred in the dark at RT under nitrogen. After 3 days, the mixture was filtered and the solution was concentrated in a rotary evaporator. The residue was chromatographed on silica gel with n-heptane as mobile phase and afforded a colorless oil (21.7 g, 82%).

Workup

  1. customto form an orange solution
  2. stirringwas then stirred in the dark at RT under nitrogen
  3. filtrationthe mixture was filtered
  4. concentrationthe solution was concentrated in a rotary evaporator
  5. customThe residue was chromatographed on silica gel with n-heptane as mobile phase

Sources & evidence

ORD record
ord-b6c79297801249f9ad8abeff96178557
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863280B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes