Water → HCID 70156854, compound

HRID 2227490Notes

Reaction equation

HRID 2227490 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13](=[O:23])[N:14]([CH3:22])[CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:7][CH:6]=1)(=O)C.O.[OH-].[K+]>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([N:14]([CH3:22])[CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:23])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 18473809HCID 18473809, compound

Product 1

HCID 70156854HCID 70156854, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.50 g of 4-[(E)-2-[N-methyl-N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl acetate was dissolved in 10 ml methanol, and then stirred with 1 ml of water and 0.36 g of potassium hydroxide at room temperature for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, the residue was neutralized with diluted hydrochloric acid, extracted with ethyl acetate, washed with water, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a residue, which was then purified via column chromatography on silica gel (dichloromethane:methanol=30:1) to provide (E)-3-(4-hydroxyphenyl)-N-methyl-N-(3-pyridylmethyl)-2-propenoic acid amide (1.00 g).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give a residue, which
  7. customwas then purified via column chromatography on silica gel (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-30966adb6c5e47608603618039fd3e28
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

Loading…