Sodium Methoxide → 2-Methoxy-3-nitro-5-tert-butyl pyridine

HRID 1744852Notes

Reaction equation

HRID 1744852 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][N:3]=1.[CH3:15][O-:16].[Na+]>CO>[CH3:15][O:16][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 222177285-Tert-butyl-2-chloro-3-nitro-pyridine

Product 1

HCID 222177832-Methoxy-3-nitro-5-tert-butyl pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-3-nitro-5-tert-butyl pyridine (30 mg, 0.14 mmol) in anhydrous MeOH (1.5 mL) under nitrogen was added a solution of sodium methoxide (1.57 g sodium in 40 mL anhydrous MeOH) (85 uL, 0.14 mmol). The reaction was heated in a sealed tube in an oil bath set at 80–90° C. overnight. The volatiles were removed in vacuo, the residue taken up in EtOAc (15 mL), washed with water (10 mL), brine (10 mL), dried (magnesium sulfate), filtered and evaporated to dryness. Flash chromatography of the residue on silica gel (10% EtOAc in hexanes) gave the desired 2-methoxy-3-nitro-5-tert-butyl pyridine as a glassy yellow solid (12 mg, 0.057 mmol, 41%).

Workup

  1. temperatureThe reaction was heated in a sealed tube in an oil bath
  2. customThe volatiles were removed in vacuo
  3. washwashed with water (10 mL), brine (10 mL)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-960cb192eb7946928bb844989ed32688
Source dataset
uspto-grants-2006_03
Patent number
US07019006B2

Reaction notes

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