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

HRID 389185Notes

Reaction equation

HRID 389185 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 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl benzoylacetate (30 g, 156 mmol) and methylamine (2 M in THF, 390 mL, 780 mmol) in EtOH (150 mL), was added acetic acid (44.7 mL, 780 mmol). The reaction mixture was heated to reflux with stirring for 15 hours. The reaction mixture was cooled, concentrated and partitioned between DCM and 1M HCl. The phases were separated and the organic layer dried over Na2SO4, filtered and concentrated to give the title compound (32 g), used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. custompartitioned between DCM and 1M HCl
  6. customThe phases were separated
  7. dry with materialthe organic layer dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f825a33b781840bdab0fb261e98bda8e
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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