Phosphorus oxychloride → 4-Chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile

HRID 506150Notes

Reaction equation

HRID 506150 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]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488756HCID 178488756, compound

Product 1

HCID 251297854-Chloro-5-(3,4-dimethoxyphenyl)nicotinonitrileYield 91%

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

  1. customthe layers separated
  2. dry with materialThe organic layer was dried over magnesium sulfate (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-87e164e4b2cc4e7580299254e064002c
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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