Sodium hydride → 4-Cyclopropylmethoxy-2-methylpyridine-1-oxide

HRID 1085106Notes

Reaction equation

HRID 1085106 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([N+]([O-])=O)[CH:7]=[CH:6][N+:5]=1[O-:13].[CH:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1>>[CH:14]1([CH2:17][O:18][C:8]2[CH:7]=[CH:6][N+:5]([O-:13])=[C:4]([CH3:3])[CH:9]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 75644Cyclopropanemethanol2×HCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxide

Product 1

HCID 107024944-Cyclopropylmethoxy-2-methylpyridine-1-oxide

Conditions

Temperature
90 °C

Procedure

To sodium hydride (55% pure) (4.4 g, 0.1 mol) (washed with petroleum ether), cyclopropyl-methanol (50 ml) was added. Then a solution of 2-methyl-4-nitropyridine-N-oxide (6.5 g, 0.042 mol) in cyclopropylmethanol (30 ml) was added during about 1 h. The dark brown mixture was heated to 90° C. and stirred at 90° C. for about 1 h. Thereafter the cyclopropylmethanol was distilled off under reduced pressure and methylene chloride (100 ml) was added to the residue. The mixture was stirred for about 30 minutes, then filtered and concentrated which gave 9.5 g of crude material.

Workup

  1. distillationThereafter the cyclopropylmethanol was distilled off under reduced pressure and methylene chloride (100 ml)
  2. additionwas added to the residue
  3. stirringThe mixture was stirred for about 30 minutes
  4. filtrationfiltered
  5. concentrationconcentrated which

Sources & evidence

ORD record
ord-1bec07b16dee45f094af34dffcffa9d8
Source dataset
uspto-grants-1991_04
Patent number
US05008278

Reaction notes

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