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

HRID 728636Notes

Reaction equation

HRID 728636 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-b74b8e032f1e4137bcf402d58f7bbbb6
Source dataset
uspto-grants-1991_09
Patent number
US05049674

Reaction notes

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