Acetic Acid → (Z)-Ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate

HRID 75540Notes

Reaction equation

HRID 75540 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=[C:5]([O:17][CH3:18])[N:4]=1.[NH2:19][CH2:20][CH2:21][OH:22].C(O)(=O)C>CCO>[CH3:1][O:2][C:3]1[C:8](/[C:9](/[NH:19][CH2:20][CH2:21][OH:22])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=[C:5]([O:17][CH3:18])[N:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 700EthanolamineHCID 86684676HCID 86684676, compound

Product 1

HCID 86684678(Z)-Ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-oxopropanoate (500 mg, 1.97 mmol) in EtOH (4 mL) was added 2-aminoethanol (0.60 mL, 9.9 mmol) followed by acetic acid (0.63 mL, 9.9 mmol). The reaction mixture was heated to 90° C. for 16 hours, cooled to room temperature and concentrated in vacuo. The residue was partitioned between EtOAc and water. The organic layer was concentrated in vacuo and the crude material was purified by chromatography on silica eluting with 20-80% EtOAc/heptane to provide the title compound (573 mg, 98%) as a clear gum.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe crude material was purified by chromatography on silica eluting with 20-80% EtOAc/heptane

Sources & evidence

ORD record
ord-35cc8f575c364a3fb971bdf404f46530
Source dataset
uspto-grants-2014_09
Patent number
US08835449B2

Reaction notes

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