3-Methoxyaniline → N-(3-methoxyphenyl)-3-phenylprop-2-enamide

HRID 1750078Notes

Reaction equation

HRID 1750078 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:17][C:1](=[O:10])[CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 108243-MethoxyanilineHCID 11430Potassium CarbonateHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 583041N-(3-methoxyphenyl)-3-phenylprop-2-enamideYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of cinnamoyl chloride (4.25 g, 25.6 mmol) in acetone (25 mL) was added to a solution of 3-methoxyaniline (2.74 mL, 24.4 mmol) and anhydrous K2CO3 (3.7 g, 26.8 mmol) in acetone-ice (28 mL-28 g) and the resulting reaction mixture was stirred at rt for 3 h. The reaction mixture was then poured into ice water, filtered, and washed with water. Recrystallization from EtOH gave N-(3-methoxyphenyl)cinnamamide (intermediate 13) (4.56 g, 74%) as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. filtrationfiltered
  3. washwashed with water
  4. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-ffe35b546abd4a2ba53a3c3d92855ac5
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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