Water → HCID 57847047, compound

HRID 550271Notes

Reaction equation

HRID 550271 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:16])[C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1.[H-].[Na+].[CH3:19]I.O>CN(C=O)C>[CH3:19][O:1][CH2:2][CH2:3][N:4]([CH3:16])[C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10242689HCID 10242689, compound

Product 1

HCID 57847047HCID 57847047, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-[(2-hydroxyethyl) (methyl)amino]benzoate (611 mg, 2.74 mmol) in DMF (10 ml) were added sodium hydride (60% in oil, 143 mg, 3.56 mmol) and methyl iodide (0.222 ml, 3.56 mmol), and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1:0-7:3, v/v) to give the title compound (467 mg, 72%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. washeluted with hexane-ethyl acetate (1:0-7:3

Sources & evidence

ORD record
ord-5a4f0c1d31a34b919e2e8cd80bf2c403
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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