Chloride → 4-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine

HRID 395417Notes

Reaction equation

HRID 395417 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1.[Cl-:21]>C(Cl)(Cl)Cl>[Cl:21][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 312ChlorideHCID 161259364-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine

Product 1

HCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine (19.18 g) was dissolved in chloroform (100 mL), and to the solution thinly chloride (10.2 mL) was added at 0° C. After 30 minutes, the mixture was warmed to room temperature and stirred for 4 hours. The reaction mixture was washed with aqaueous saturated sodium hydrogendcarbonate and brine, dried over anhydrous sodium sulfate and evaporated. The residue was then recrystallized from ethyl acetate-hexane to give the title compound as pale yellow crystalline powder.

Workup

  1. washThe reaction mixture was washed with aqaueous saturated sodium hydrogendcarbonate and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe residue was then recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-043392e7ce534f2fb978232d23271a64
Source dataset
uspto-grants-2003_08
Patent number
US06605620B1

Reaction notes

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