Methanol → Methyl 6-chloropyridine-3-carboxylate

Temperature

60 °C

An oven-dried, 500 milliliter (mL) round bottom flask (“RBF”) was charged with 6-chloronicotinic acid (compound 1) (14.4 grams (g), 91.3 millimole (mmol)), in 200 mL of freshly distilled MeOH. H2SO4 (1.22 mL, 22.8 mmol) was added dropwise to this mixture at room temperature. The mixture was stirred for 6 hours at 60° C. The organic phase was separated and extracted with ethyl acetate at pH 8. The organics were then combined and dried over Na2SO4. After filtering the mixture, the solvent was evaporated to obtain the crude product. The resulting crude product was then purified by silica gel column chromatography (eluent: methylene chloride:hexane=1:10 v/v) to yield 10.5 g (73%) of methyl 6-chloronicotinate (Compound 2).

1. customThe organic phase was separated
2. extractionextracted with ethyl acetate at pH 8
3. dry with materialdried over Na2SO4
4. filtrationAfter filtering the mixture
5. customthe solvent was evaporated
6. customto obtain the crude product
7. customThe resulting crude product was then purified by silica gel column chromatography (eluent: methylene chloride:hexane=1:10 v/v)

ORD record

ord-968429335d7b4176ba5fb8b0eb3708c8

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420231B2