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

HRID 1891345Notes

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 rt, 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-4988ead6478f4d02a3e8b127c35dd5e9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507536B2

Reaction notes

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