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

HRID 984146Notes

Reaction equation

HRID 984146 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-b18bc9898168494fa55e1fabc5235296
Source dataset
uspto-grants-2005_03
Patent number
US06867221B2

Reaction notes

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