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

HRID 2045695Notes

Reaction equation

HRID 2045695 reaction equation
C(O)(=O)C.[C:5]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:19][NH2:20]>CCO>[CH3:19][NH:20][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

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

Acetic acid (44.7 mL, 780 mmol) was added to a solution of ethyl benzoylacetate (30 g, 156 mmol) and methyl amine (2M in THF, 390 mL, 780 mmol) in EtOH (150 mL). The reaction mixture was heated to reflux and stirred for 15 h. The reaction mixture was concentrated and partitioned between DCM and 1M HCl. The layers were separated, and the organic layer was dried over Na2SO4, filtered and concentrated to give the title compound (32 g, 99% yield) which was used with no further purification.

Workup

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

Sources & evidence

ORD record
ord-17c7ff3806244b91bb08d6807e4e854c
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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