Methanol → 2-Methoxy-3-nitro-5-ethyl-6-methylpyridine

HRID 1033005Notes

Reaction equation

HRID 1033005 reaction equation
[Na].Cl[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH2:12][CH3:13])=[C:5]([CH3:14])[N:4]=1.[CH3:15][OH:16]>C(OCC)C>[CH3:15][O:16][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH2:12][CH3:13])=[C:5]([CH3:14])[N:4]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 103755472-Chloro-5-ethyl-6-methyl-3-nitropyridine

Product 1

HCID 104652702-Methoxy-3-nitro-5-ethyl-6-methylpyridineYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Sodium metal (100 mg, 4.3 mmol) was dissolved in methanol (5 mL) under a nitrogen atmosphere. A solution of 2-chloro-3-nitro-5-ethyl-6-methylpyridine (677 mg, 3.37 mmol) in methanol (5 mL) was added dropwise. The reaction was warmed at 50° C. for four hours. The reaction was cooled, diluted with diethyl ether, the ether layer washed with water, dried (Na2SO4), filtered through a pad of charcoal and evaporated to yield 535 mg (80%) of product.

Workup

  1. temperatureThe reaction was cooled
  2. washthe ether layer washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through a pad of charcoal
  5. customevaporated

Sources & evidence

ORD record
ord-5cc1a9aad7fe434096b3070cd9bc941f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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