Ammonium Chloride → 2-Methoxy-4-methyl-5-nitropyridine

HRID 1398774

Reaction equation

HRID 1398774 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O-:13].[Na+].[Cl-].[NH4+]>CO>[CH3:12][O:13][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 2431692-Methoxy-4-methyl-5-nitropyridineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-4-methyl-5-nitropyridine (3.0 g, 17.3 mmol) in methanol (20 mL) was added a solution of sodium methoxide (28% in methanol, 10 mL) dropwise at 0° C. The mixture was warmed to room temperature and stirred for 16 hr. The mixture was neutralized by addition of aqueous ammonium chloride and concentrated in vacuo. The residue was dissolved in water and extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (2.84 g, 16.8 mmol, 98%) as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washOrganic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5af145c853f74bec9de396d8d7a0df88
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Linked notes

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