Methanol → Methyl 3-bromoisonicotinate Hydrochloride

To a stirred suspension of 3-bromoisonicotinic acid hydrochloride (27.4 g, 0.10 mol) in ethyl acetate (250 ml) was added one drop of DMF followed by thionyl chloride (18.5 g, 0.16 mol). The mixture was heated at reflux for 1 h and allowed to cool to room temperature. The mixture was then concentrated under reduced pressure to give an off-white solid. To this was added methanol and this was refluxed for 2 hrs. The mixture was then concentrated under reduced pressure and diluted with ethyl acetate. The precipitate was collected on filter paper on a Buchner funnel. The white solid was washed with ethyl acetate and air-dried. The white solid was placed in a vacuum oven at 60° C. overnight with a nitrogen bleed. Yield: 18.5 g (71% th).

1. temperatureThe mixture was heated
2. temperatureat reflux for 1 h
3. concentrationThe mixture was then concentrated under reduced pressure
4. customto give an off-white solid
5. temperaturethis was refluxed for 2 hrs
6. concentrationThe mixture was then concentrated under reduced pressure
7. additiondiluted with ethyl acetate
8. customThe precipitate was collected
9. filtrationon filter paper on a Buchner funnel
10. washThe white solid was washed with ethyl acetate
11. customair-dried

ORD record

ord-ee3d9598f4ed4ca8a6b52ecc878e2b0a

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709677B2