Methyl iodide → HCID 18694294, compound

HRID 1870886Notes

Reaction equation

HRID 1870886 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH:10]([CH3:13])[C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=1.[C:24](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH:10]([CH3:13])[C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18694262HCID 18694262, compound

Product 1

HCID 18694294HCID 18694294, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 2'-methyl-4'-(3-methyl-2-oxopyrrolidin-1-yl)biphenyl-4-carboxylic acid (D21, 0.35 g, 0.0011 mole) in DMF (5 ml) at 25° C. was treated with anhydrous potassium carbonate (0.27 g, 0.0020 mole) and iodomethane (0.08 ml, 0.0014 mole). The mixture was stirred for 3 hours, then diluted with water (100 ml) and extracted with ethyl acetate (2×100 ml). The combined extract was washed with water (2×100 ml), then dried (Na2SO4) and concentrated in vacuo to afford the title compound as a beige solid (0.35 g, 99%).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. extractionThe combined extract
  3. washwas washed with water (2×100 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c31adf460fe94120a6e87f2939f82bf6
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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