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

HRID 1774836Notes

Reaction equation

HRID 1774836 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 hours, the mixture was washed with water and then hydrochloric acid (2 N, aqueous). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford title compound (10.9 g, yield: 90%) as an oil. MS: 202.1 (M+H+)+.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-598266233b4047029e5ceb147f5e0f3b
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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