Water → ethyl 4-(N-methylpropionamido)cinnamate

HRID 726288Notes

Reaction equation

HRID 726288 reaction equation
[H-].[Na+].[C:3]([NH:7][C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=1)(=[O:6])[CH2:4][CH3:5].I[CH3:22].O>CN(C)C=O>[CH3:22][N:7]([C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=1)[C:3](=[O:6])[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54078953Ethyl 4-propionamidocinnamate

Product 1

HCID 53960793ethyl 4-(N-methylpropionamido)cinnamateYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% active, 31 mg) in dimethylformamide (1 ml) was added a solution of ethyl 4-propionamidocinnamate (160 mg) in dimethylformamide (2 ml) at ambient temperature under nitrogen atmosphere. The mixture was stirred for 1 hour at same temperature, and a solution of iodomethane (111 mg) in dimethylformamide (2 ml) was added thereto. The reaction mixture was stirred at same temperature for 2 hours, poured into water, and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give ethyl 4-(N-methylpropionamido)cinnamate (168 mg) as an oil.

Workup

  1. stirringThe reaction mixture was stirred at same temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea5ecd6823ba41c088d2299123e8e8ef
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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