1,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile → 2-Chloro-6-methyl-5-phenylnicotinonitrile

HRID 1085474

Reaction equation

HRID 1085474 reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]([CH3:15])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)#[N:2].C1(P(Cl)([Cl:25])=O)C=CC=CC=1>>[Cl:25][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:15])[N:5]=1

Participants

3

Reactant 2

HCID 202311,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrileHCID 69990Phenylphosphonic dichloride

Product 1

HCID 14763652-Chloro-6-methyl-5-phenylnicotinonitrileYield 85%

Procedure

A mixture of 100.34 g 3-cyano-6-methyl-5-phenyl-1H-pyridin-2-one [Walker and Weaver, J. Org. Chem. 26, 4441 (1961)] and 192 ml phenylphosphonic dichloride (C6H5POCl2) was warmed to 160°-170° C. and kept at that temperature for about 16 hours. The reaction mixture was cooled and poured into ice water. The solid product was collected, dried in a vacuum oven and extracted with ether. The ether solution was concentrated, and the residue was washed with hexane and extracted with 300 ml 15% aqueous potassium bicarbonate. The resulting solid was dried in a vacuum oven to give 92.71 g (85%) 2-chloro-3-cyano-6-methyl-5-phenylpyridine, m.p. 134°-135° C.

Workup

  1. temperaturewas warmed to 160°-170° C.
  2. temperatureThe reaction mixture was cooled
  3. customThe solid product was collected
  4. customdried in a vacuum oven
  5. extractionextracted with ether
  6. concentrationThe ether solution was concentrated
  7. washthe residue was washed with hexane
  8. extractionextracted with 300 ml 15% aqueous potassium bicarbonate
  9. customThe resulting solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-778b9871528946f18e36b335d199c984
Source dataset
uspto-grants-1991_04
Patent number
US05010086

Linked notes

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