Hydrochloric Acid → 5-Bromo-4-isobutoxy-2-methylpyridine 1-oxide

HRID 709623Notes

Reaction equation

HRID 709623 reaction equation
[Br:1][C:2]1[C:3]([N+]([O-])=O)=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1.[H-].[Na+].Cl.[CH3:16][CH:17]([CH3:20])[CH2:18][OH:19]>>[Br:1][C:2]1[C:3]([O:19][CH2:18][CH:17]([CH3:20])[CH3:16])=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6560IsobutanolHCID 24758Sodium hydrideHCID 123329085-Bromo-2-methyl-4-nitropyridine 1-oxide

Product 1

HCID 1177597255-Bromo-4-isobutoxy-2-methylpyridine 1-oxide

Procedure

Under a nitrogen atmosphere, to a solution of 5-bromo-2-methyl-4-nitropyridine 1-oxide (4.10 g) in 2-methyl-1-propanol (80 mL) was added 60% sodium hydride (2.69 g) at 0° C., and the mixture was stirred for 2 hr. 6N Hydrochloric acid was added to the reaction mixture, and the resulting brown solid was filtered off. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (3.40 g) as a pale-yellow solid.

Workup

  1. filtrationthe resulting brown solid was filtered off
  2. customThe solvent in the filtrate was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-455285d3579849e99663430abae09f91
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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