Hydrochloric Acid → 2-(Chloromethyl)-4-phenylpyridine--hydrogen chloride (1/1)

HRID 1196522Notes

Reaction equation

HRID 1196522 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([CH2:13]O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:15]>CCOCC>[ClH:15].[Cl:15][CH2:13][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12217651(4-PHENYLPYRIDIN-2-YL)METHANOL

Product 1

HCID 198988332-(Chloromethyl)-4-phenylpyridine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-phenyl-2-pyridinemethanol (1.57 g) in ether (5 ml) was treated with ethereal hydrogen chloride (ca 5 ml). The resulting solid was filtered off and added to redistilled thionylchloride (7.5 ml) at ca 0°. The brown solution was stirred at ca 0° for 2 h and at 22° for 0.5 h. Ether (100 ml) was added and the resulting solid was filtered off to give the title compound as a solid (1.81 g). T.l.c. Silica (Dichloromethane, ethanol and ammonia 200:8:1) Rf 0.7.

Workup

  1. filtrationThe resulting solid was filtered off
  2. additionadded
  3. distillationto redistilled thionylchloride (7.5 ml) at ca 0°
  4. additionEther (100 ml) was added
  5. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-d79316fabce34fe8b2b4218efad80afd
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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