Ammonium Hydroxide → 2-Chloro-3-phenylpyridine

HRID 845200Notes

Reaction equation

HRID 845200 reaction equation
[C:1]1([C:7]2[C:8](=O)[NH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:16])=O.[OH-].[NH4+]>>[Cl:16][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 27628082-Hydroxy-3-phenylpyridine

Product 1

HCID 27628072-Chloro-3-phenylpyridineYield 31%

Procedure

A solution of 3-phenyl-2-(1H)-pyridone (VIII; 20.0 g, 0.12 mole) and phosphorus oxychloride (300 mL) was refluxed for 6 hr and then slowly poured over crushed ice (300 mL). The resulting solution was made basic with ammonium hydroxide which led to formation of a precipitate. The mixture was extracted with ethyl ether (3×500 mL) and the combined organic extracts were dried (Na2SO4). Concentration in vacuo gave a solid which was recrystallized from ethyl acetate to yield 7.0 g (31%) of 2-chloro-3-phenylpyridine (VI), m.p. 52°-56°.

Workup

  1. additionslowly poured
  2. extractionThe mixture was extracted with ethyl ether (3×500 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. concentrationConcentration in vacuo
  5. customgave a solid which
  6. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2a83bd9093e844c79b47cee2eb7586df
Source dataset
uspto-grants-1988_07
Patent number
US04757073

Reaction notes

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