Pyridine → N-(4-fluorophenyl)acetamide
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- concentrationthe mixture was concentrated in vacuo
- additionthe residue was diluted with cold water
- filtrationThe resulting precipitate was filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-e2199747741544279ac642f150d5786b
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658637B2
Reaction notes
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