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

HRID 1848566Notes

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.[ClH:13]>>[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 123329085-Bromo-2-methyl-4-nitropyridine 1-oxide

Product 1

HCID 136827785-Bromo-4-chloro-2-methylpyridine 1-oxide

Procedure

5-Bromo-2-methyl-4-nitropyridine oxide (7.0 g, 30 mmol) was refluxed in conc. HCl (80 mL) for 16 hrs. The mixture was allowed to cool to room temperature, partially concentrated and then neutralized by NaOH (10N) to pH 7. The crude was partitioned between CHCl3 and water. The organic solution was separated, dried and concentrated to yield 5-bromo-4-chloro-2-methylpyridine oxide as a white solid (6.71 g). MS [M+H]+: 223.7; tR=1.91 min. (method 1).

Workup

concentrationpartially concentrated
customThe crude was partitioned between CHCl3 and water
customThe organic solution was separated
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-4195eae954ed4add950919fa9ea96f04
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952161B2

Reaction notes

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