Methyl iodide → HCID 19418505, compound

HRID 1648714Notes

Reaction equation

HRID 1648714 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=2)[C:6]([CH3:20])=[C:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[C:4]=1[OH:32].I[CH3:34]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][C:12]([C:13]2[CH2:18][CH:17]=[CH:16][N:15]([CH3:34])[CH:14]=2)=[O:19])[C:6]([CH3:20])=[C:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[C:4]=1[OH:32]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 19418500HCID 19418500, compound

Product 1

HCID 19418505HCID 19418505, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dimethoxy-6-(10-hydroxydecyl)-5-methyl-4-nicotinoyloxyphenol (1.1 g) was dissolved in dimethylformamide (5 ml). Iodomethane (0.3 ml) was added, and the mixture was allowed to react at room temperature for 16 hours. After concentration under reduced pressure, the residue was dissolved in ethyl acetate (20 ml). Water (20 ml) containing sodium hydrosulfite (1.74 g) and sodium bicarbonate (1.26 g) was added, and the mixture was stirred at room temperature for 1 hour. The organic layer was concentrated under reduced pressure, and the residue was subjected to column chromatography on silica gel and eluted with ethyl acetate to obtain the desired compound (1.1 g) as an oil.

Workup

  1. customto react at room temperature for 16 hours
  2. concentrationAfter concentration under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  4. additionWater (20 ml) containing sodium hydrosulfite (1.74 g) and sodium bicarbonate (1.26 g)
  5. additionwas added
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-987fabdbd9f04843a695fe941eb0f8ff
Source dataset
uspto-grants-1995_07
Patent number
US05436359

Reaction notes

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