1-(6-Chloropyridin-3-yl)ethan-1-one → 5-Acetyl-2-methoxypyridine

HRID 633752Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 15 mL of methanol, 500 mg (2.89 mmol) of 1-(6-chloropyrid-3-yl)ethanone and 1.17 g (21.69 mmol) of sodium methoxide is heated in a microwave reactor at 160° C. for 4 hours. The reaction medium is evaporated to dryness. After purification by chromatography on silica gel (eluent A/B: heptane/EtOAc, gradient A/B: t 0 min 0% B, t 5 min 20% B, t 30 min 40% B), 230 mg of 1-(6-methoxypyrid-3-yl)ethanone were obtained, corresponding to the following characteristics:

Workup

customThe reaction medium is evaporated to dryness
customAfter purification by chromatography on silica gel (eluent A/B: heptane/EtOAc, gradient A/B: t 0 min 0% B, t 5 min 20% B, t 30 min 40% B), 230 mg of 1-(6-methoxypyrid-3-yl)ethanone
customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record: ord-b06403fd61fb40668660ba0ae8da4c11
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321790B2

Reaction notes

Loading…