Acetic Acid → (Z)-methyl 3-(2,4-dimethoxyphenyl)-3-((2-hydroxyethyl)amino)acrylate
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(O)(=O)C.[CH2:22]([CH2:24][NH2:25])[OH:23]>CC(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[C:11](/[NH:25][CH2:24][CH2:22][OH:23])=[CH:12]/[C:13]([O:15][CH3:16])=[O:14]Participants
Conditions
- Temperature
- 83 °C
Procedure
To a mixture of methyl 3-(2,4-dimethoxyphenyl)-3-oxopropanoate (3.50 g, 14.69 mmol) and acetic acid (0.17 mL, 2.94 mmol) in i-PrOH (70 mL) was added ethanolamine (0.88 mL, 14.69 mmol) and the reaction mixture was heated to 83° C. Additional ethanolamine (0.88 mL, 14.69 mmol) was added to the reaction mixture at two, four and six hours. After stirring at 80° C. for 48 hours, the reaction mixture was cooled and concentrated under reduced pressure before the residue was suspended in equal parts of a saturated sodium bicarbonate solution and water under N2. After stirring overnight, the solids were collected by vacuum filtration and dried in a vacuum oven at 30° C. overnight to afford the title compound (2.72 g, 63%) as a beige colored power.
Workup
- temperaturethe reaction mixture was cooled
- concentrationconcentrated under reduced pressure before the residue
- stirringAfter stirring overnight
- filtrationthe solids were collected by vacuum filtration
- customdried in a vacuum oven at 30° C. overnight
Sources & evidence
- ORD record
- ord-87dbaacf1b86412eb9a8aea123b1f8b3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841314B2
Reaction notes
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