Acetic Acid → Ethyl 3-(methylamino)-3-phenylacrylate

HRID 1879269Notes

Reaction equation

HRID 1879269 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][NH2:16].C(O)(=O)C>CCO>[CH3:15][NH:16][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6329MethylamineHCID 7170Ethyl benzoylacetate

Product 1

HCID 58005139Ethyl 3-(methylamino)-3-phenylacrylateYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl benzoylacetate and methylamine (2M in THF, 8 eq.) in EtOH (1 M) was added acetic acid (8 eq.). The reaction mixture was heated to reflux and stirred for three days. The reaction mixture was concentrated and partition between DCM and 1N HCl. The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated to give the title compound 112 (20%) which was used with no further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. custompartition between DCM and 1N HCl
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dc5ed1a494244fd988252b8f61b6b4d3
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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