2-Chloro-4-methoxypyridine → 2,4-dimethoxypyridine

HRID 1948239Notes

Reaction equation

HRID 1948239 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1>>[CH3:1][O:2][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 19911282-Chloro-4-methoxypyridineHCID 10942334Sodium Methoxide

Product 1

HCID 8177312,4-dimethoxypyridineYield 59.4%

Procedure

According to Scheme 23 Step 1: To a solution of sodium methoxide (30% in MeOH, 2 eq, 35 mmol) was added 2-chloro-4-methoxypyridine (1 eq, 17.0 mmol, 2.50 g). The reaction was refluxed overnight. The reaction was allowed to cool, poured onto water (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure to afford 2,4-dimethoxypyridine (10.1 mmol, 1.40 g, 58%) as a colorless oil. The crude product was reacted on.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. temperatureto cool
  3. additionpoured onto water (10 mL)
  4. extractionextracted with CH2Cl2 (3×10 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59b427d9e1084a58873db065a926b4a0
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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