Ethyl chloroacetate → HCID 86757569, compound

HRID 428142Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:21])[CH2:9][NH:10][C:11](=[O:20])/[CH:12]=[CH:13]/[C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:21][CH:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:9][NH:10][C:11](=[O:20])/[CH:12]=[CH:13]/[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(E)-N-[2-(3-hydroxyphenyl)-2-hydroxyethyl]-3-(3-pyridyl)-2-propenoic acid amide (5.68 g, 20 mmol) and ethyl chloroacetate (5.2 ml, 48 mmol) were dissolved in dimethylformamide (60 ml) and potassium carbonate (8.28 g, 60 mmol) was added and stirred at 50° C. for 7 hours. After allowing to cool, insoluble materials were filtered out and water was added to the filtrate, extracted with ethyl acetate and dried over magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:hexane:methanol=20:2:1) and dried under reduced pressure to yield the titled compound (3.80 g, 51%).

Workup

temperatureto cool
filtrationinsoluble materials were filtered out and water
additionwas added to the filtrate
extractionextracted with ethyl acetate
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled out under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform:hexane:methanol=20:2:1)
customdried under reduced pressure

Sources & evidence

ORD record: ord-6d457dfa486645fd84a55e880f055aba
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313153B1

Reaction notes

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