Picolyl chloride → HCID 15166213, compound

HRID 727891Notes

Reaction equation

HRID 727891 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N+:10]([O-:13])=[C:9]([CH3:14])[C:8]=1[CH3:15].Cl[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>O1CCCC1>[CH3:14][C:9]1[C:8]([CH3:15])=[C:7]([O:6][CH2:5][CH2:4][O:3][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:12]=[CH:11][N+:10]=1[O-:13]

Participants

5

Reactant 3

HCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 15166210HCID 15166210, compound

Product 1

HCID 15166213HCID 15166213, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.39 g of 60% sodium hydride was added to a suspension of 1.20 g (6.5 mmol) of 4-(2-hydroxyethoxy)-2,3-dimethylpyridine N-oxide in 40 ml of tetrahydrofuran under cooling with ice in a nitrogen atmosphere to obtain a mixture. This mixture was stirred for 0.5 hour, followed by the addition of 0.83 g (6.5 mmol) of 2-chloromethylpyridine. The obtained mixture was heated under reflux for 8 hours, cooled and filtered. The filtrate was concentrated and purified by silica gel column chromatography (solvent: ethyl acetate/n-hexane=4:1~CHCl3 /MeOH=19:1) to obtain 0.61 g of 2,3-dimethyl-4-(2-pyridylmethoxyethoxy)pyridine N-oxide.

Workup

  1. temperatureunder cooling with ice in a nitrogen atmosphere
  2. customto obtain a mixture
  3. temperatureThe obtained mixture was heated
  4. temperatureunder reflux for 8 hours
  5. temperaturecooled
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography (solvent: ethyl acetate/n-hexane=4:1~CHCl3 /MeOH=19:1)

Sources & evidence

ORD record
ord-2c97d1af055d43398d9270a01bade92b
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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