Pyridine → 3-chloro-N-(2-fluorophenyl)propanamide

HRID 530330Notes

Reaction equation

HRID 530330 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.[Cl:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>ClCCCl>[Cl:15][CH2:16][CH2:17][C:18]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[F:1])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 95842-FluoroanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 42560293-chloro-N-(2-fluorophenyl)propanamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-fluoroaniline (6.67 g, 60 mmol) and pyridine (5.21 g, 66 mmol) in 1,2-dichloroethane (50 mL) was added 3-chloropropionyl chloride (8.38 g, 66 mmol) dropwise at 15° C. After stirring at room temperature for 2 hr, the mixture was washed with water and then 2N aq. hydrochloric acid. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to afford title compound (10.9 g, 90% yield) as an oil. MS: 202.1 (M+H)+.

Workup

  1. washthe mixture was washed with water
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41c4379a553f4f89ad105f81cabe4622
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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