Sodium Methoxide → 4-methoxy-2-n-propylpyridine-N-oxide

HRID 1421260Notes

Reaction equation

HRID 1421260 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[C:6]([CH2:11][CH2:12][CH3:13])[CH:5]=1)([O-])=O.[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[C:6]([CH2:11][CH2:12][CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 187069664-nitro-2-n-propylpyridine-N-oxide

Product 1

HCID 187069924-methoxy-2-n-propylpyridine-N-oxideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-nitro-2-n-propylpyridine-N-oxide (146.0 g, 0.8 mol) in 500 ml of anhydrous methanol was stirred and 190 ml of a 4.6 M methanolic sodium methoxide solution was added dropwise. When the addition was complete, the mixture was stirred for three hours. The precipitated sodium nitrite was filtered off and washed with methanol. The filtrate was evaporated and the residue was stirred with 300 ml of dichloromethane. The mixture was filtered and evaporated to afford 129 g (97%) of 4-methoxy-2-n-propylpyridine-N-oxide as an oil. 1H-NMR (CDCl3, 200 MHz) δ: 1.07 (t, 3H), 1.80 (sext, 2H), 2.80 (t, 2H), 3.87 (s, 3H), 6.66-6.78 (m, 2H), 8.17 (d, 2H).

Workup

  1. additionWhen the addition
  2. filtrationThe precipitated sodium nitrite was filtered off
  3. washwashed with methanol
  4. customThe filtrate was evaporated
  5. stirringthe residue was stirred with 300 ml of dichloromethane
  6. filtrationThe mixture was filtered
  7. customevaporated

Sources & evidence

ORD record
ord-2471a284523940d5964186b8ce6cda0a
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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