Methyl iodide → HCID 68525615, compound

HRID 884094Notes

Reaction equation

HRID 884094 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]=[CH:7][C:8]=1[N:9]([CH3:28])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68525456HCID 68525456, compound

Product 1

HCID 68525615HCID 68525615, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-[3-methoxy-4-(5-nitropyridin-2-ylamino)phenyl]propionate (3.70 g, 11 mmol) in DMF (60 mL) were added under ice-cooling sodium hydride (60%, 490 mg, 12 mmol) and methyl iodide (0.77 mL, 12 mmol), and the resulting reaction solution was stirred for 2 hours gradually warming up to room temperature. The reaction solution was concentrated under reduced pressure. To the residue was added ethyl acetate, washed with water and brine, and then dried with anhydrous magnesium sulfate. The solvent was evaporated, to thereby yield 4.27 g of the title compound.

Workup

  1. customthe resulting reaction solution
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e7ca97b6b22c4e369558c4d7b134e644
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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