Pyridine → N-(4-fluorophenyl)acetamide

HRID 244466

Reaction equation

HRID 244466 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:17])[CH3:16]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:15](=[O:17])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 97314-Fluoroaniline

Product 1

HCID 9601N-(4-fluorophenyl)acetamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (ice-bath) solution of 4-fluorophenylamine (2.9 mL, 30 mmol) and anhydrous pyridine (3.7 mL, 45 mmol) in methylene chloride (50 mL) was slowly added a solution of acetyl chloride (2.4 mL, 33 mmol) in methylene chloride (10 mL). After 15 minutes, the mixture was concentrated in vacuo and the residue was diluted with cold water. The resulting precipitate was filtered, washed with water and dried to afford 4.2 g of N-(4-fluorophenyl)acetamide as an off white solid. MS m/z 154 (MH+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was diluted with cold water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e2199747741544279ac642f150d5786b
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Linked notes

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