Methyl iodide → HCID 19418505, compound

HRID 1734953Notes

Reaction equation

HRID 1734953 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-66bdf74d097949bd9cb5bc47c96109b9
Source dataset
uspto-grants-1996_07
Patent number
US05534639

Reaction notes

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