Ammonium Chloride → 3-Chloro-2-methoxy-4,6-dimethylpyridine

HRID 1043894Notes

Reaction equation

Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([O:10][CH3:11])=[C:6]([Cl:9])[C:7]=1[CH3:8].C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:9][C:6]1[C:5]([O:10][CH3:11])=[N:4][C:3]([CH3:12])=[CH:2][C:7]=1[CH3:8]

Participants

Conditions

Temperature: -78 °C

Procedure

3-bromo-5-chloro-6-methoxy-2,4-dimethylpyridine (930 mg) was added to THF (10 mL). The solution was cooled to −78° C., and n-butyllithium (2.6 M solution in n-hexane, 1.428 mL) was added, followed by stirring at the same temperature for one hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with DCM. The organic layer was washed with brine and dried over sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (300 mg).

Workup

extractionfollowed by extraction with DCM
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customThe desiccant was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

Sources & evidence

ORD record: ord-6c64f2a183194f179e74453f3fed0a5a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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