Ammonium Hydroxide → 2-Chloro-4,6-dimethyl-5-phenylpyridine-3-carbonitrile

HRID 1995612Notes

Reaction equation

HRID 1995612 reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]([CH3:16])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]=1[CH3:9])#[N:2].C1(P(Cl)([Cl:26])=O)C=CC=CC=1.[OH-].[NH4+]>>[Cl:26][C:4]1[C:3]([C:1]#[N:2])=[C:8]([CH3:9])[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH3:16])[N:5]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 69990Phenylphosphonic dichlorideHCID 2610864,6-Dimethyl-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 135028532-Chloro-4,6-dimethyl-5-phenylpyridine-3-carbonitrile

Procedure

3-Cyano-4,6-dimethyl-5-phenyl-2-pyridone (7.0 grams) and phenylphosphonic dichloride (12.1 grams) were heated at 175°-180° C. for 2-3 hours. The solution was cooled, poured into ice water and made basic with ammonium hydroxide. A precipitate formed which was collected, air dried, and determined by NMR to be the desired product, yield 7.6 grams, m.p. 118°-123° C.

Workup

  1. temperatureThe solution was cooled
  2. customA precipitate formed which
  3. customwas collected
  4. customair dried

Sources & evidence

ORD record
ord-b076809bd7354b92b79fd2dbc213073a
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

Loading…