Methyl iodide → 5-[(2-Methoxy-6-methylpyridin-4-yl)oxy]-N-methyl-2-nitroaniline

HRID 1843720Notes

Reaction equation

HRID 1843720 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH:19][CH3:20])[CH:11]=2)[CH:3]=1.[CH3:21]I>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH3:21][O:8][C:6]1[CH:5]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([CH:11]=2)[NH:19][CH3:20])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178482267HCID 178482267, compound

Product 1

HCID 667057765-[(2-Methoxy-6-methylpyridin-4-yl)oxy]-N-methyl-2-nitroanilineYield 90%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 6-methyl-4-[3-(methylamino)-4-nitrophenoxy]pyridin-2-ol produced in Example (17a) (7.85 g, 18.7 mmol), methyl iodide (4.66 mL, 74.8 mmol) and silver carbonate (10.32 g, 37.4 mmol) in chloroform (100 mL) was stirred in a nitrogen atmosphere at room temperature for five days. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. Then, the residue was purified by silica gel chromatography (hexane/ethyl acetate, 5:1) to obtain the title compound (4.87 g, 90%) as a yellow solid.

Workup

  1. customThe insoluble matter was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThen, the residue was purified by silica gel chromatography (hexane/ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-28e910c653ff4358a5460c7c93fc5565
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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