Pyridine → N-(2-Bromophenyl)cinnamamide

HRID 1095666

Reaction equation

HRID 1095666 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].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>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:15](=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 119922-BromoanilineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 764332N-(2-Bromophenyl)cinnamamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-bromobenzenamine (200.0 g, 1163 mmol), pyridine (188.1 ml, 2325 mmol) and dry dichloromethane (1000 ml) at 0° C. was added slowly cinnamoyl chloride (193.7 g, 1163 mmol). The resulting mixture was stirred while warming to ambient temperature overnight. The resulting mixture was washed with sodium bicarbonate (1000 ml), 10% sodium bisulfate (1000 ml), sodium bicarbonate (1000 ml) and brine (1000 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to yield title compound as a solid (172.3 gm, 98% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected.

Workup

  1. washThe resulting mixture was washed with sodium bicarbonate (1000 ml), 10% sodium bisulfate (1000 ml), sodium bicarbonate (1000 ml) and brine (1000 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-663da7ac9a59420ba1f1efdc76a512b6
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Linked notes

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