Pyridine → 3'-Methylcinnamanilide

HRID 1045353Notes

Reaction equation

HRID 1045353 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[C:4]1([CH3:8])[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:15](=[O:24])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7934m-ToluidineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 5830183'-Methylcinnamanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

m-Toluidine (5 g, 46.64 mmol) and pyridine (3.77 mL, 46.64 mmol) were dissolved in dry dichloromethane (25 mL). To the reaction mixture, cinnamoyl chloride (7.72 g, 46.64 mmol) was added and stirred for 3 h at 0° C. The reaction mixture was extracted with dichloromethane washing with water and 2N HCl. The solvent was removed and the crude product was used in the next step without further purification.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane washing with water and 2N HCl
  2. customThe solvent was removed
  3. customthe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-14ca28f2f70a417195f49f94d34eea8b
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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