Pyridine → HCID 66931798, compound

HRID 723635Notes

Reaction equation

HRID 723635 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[N:15]1[CH:20]=[CH:19]C=CC=1.[OH-].[Na+].[C:23]([O-:26])(O)=O.[Na+].[CH2:28](Cl)Cl>>[CH2:11]([O:10][C:8](=[O:9])/[CH:7]=[CH:6]/[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:26])[C:20]([NH2:15])([CH3:19])[CH3:28])=[CH:14][CH:13]=1)[CH3:12]

Participants

6

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 516892Sodium Bicarbonate

Product 1

HCID 66931798HCID 66931798, compoundYield 101%

Procedure

The acid chloride (12.778 g, 80 mmol, 1.4 equivalent) was suspended in DCM (200 mL) and ethyl 4-aminocinnamate (11.045 g, 57.7 mmol, 1 equivalent) was added. Pyridine (7.01 mL, 86.6 mmol, 1.5 equivalent) was added drop wise and the mixture was stirred for 3.5 h at room temperature. The reaction was then poured into a mixture of 1N NaOH (25 mL) and saturated aqueous NaHCO3 (100 mL) and extracted with EtOAc. The organic phase was washed with aqueous NaHCO3, water and brine, and dried over MgSO4. Removal of solvent under reduced pressure gave the title compound as a white solid (15.96 g, 101% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with aqueous NaHCO3, water and brine
  3. dry with materialdried over MgSO4
  4. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-c0273e28350d4f6d9ad7fc08d95946ed
Source dataset
uspto-grants-2006_11
Patent number
US07141574B2

Reaction notes

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