Pyridine → HCID 306500, compound

HRID 1900738Notes

Reaction equation

HRID 1900738 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:16](Cl)(=[O:25])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:16](=[O:25])[CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7732P-AnisidineHCID 8857Ethyl AcetateHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 306500HCID 306500, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

p-Anisidine (25 g, 0.203 mol) was suspended in acetone (400 ml), to which pyridine (19.7 ml, 0.244 mol) was added. While cooling on ice, cinnamoyl chloride (37.2 g, 0.223 mol) was further added, followed by stirring at ambient temperature for 20 minutes. As a result, a uniform solution was obtained. The solvent was condensed under reduced pressure. To the residue, ethyl acetate and water were added. The sediment was collected by filtration, washed with ethyl acetate and water, and dried with air. 50.4 g of the title compound was obtained as pale greenish brown powder (98.0%, mp.: 147°-150° C.).

Workup

  1. additionwas added
  2. additionwas further added
  3. customAs a result, a uniform solution was obtained
  4. customcondensed under reduced pressure
  5. filtrationThe sediment was collected by filtration
  6. washwashed with ethyl acetate and water
  7. customdried with air

Sources & evidence

ORD record
ord-4dd80b0739b04071a04cdc977281ec9a
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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