Phosphorus oxychloride → 4-Chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([C:18]=2O)[C:16]#[N:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:18]1[C:15]([C:16]#[N:17])=[CH:14][N:13]=[CH:12][C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1Participants
3
Procedure
A solution of 5-(3,4-dimethoxyphenyl)-4-hydroxynicotinonitrile (4 g, 15.7 mmol) in phosphorus oxychloride (POCl3, 25 mL) was heated at 125° C. for 1.5 h, then cooled to r.t. and poured into an ice/3 N sodium hydroxide (NaOH)/EtOAc mixture. The mixture was stirred and the layers separated. The organic layer was dried over magnesium sulfate (MgSO4), filtered and concentrated to give 4-chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile (3.9 g, 91%) as a brown solid.
Workup
- customthe layers separated
- dry with materialThe organic layer was dried over magnesium sulfate (MgSO4)