Acetonitrile → methyl 6-chloronicotinate N-oxide

温度

0 °C

To a 500 mL round bottom flask containing methyl 6-chloronicotinate (4.50 g, 26.2 mmol) was added MeCN (100 mL). The resulting mixture was then stirred at 0° C. for 10 min. At this time, urea hydrogen peroxide (4.93 g, 52.5 mmol) solid was added before the dropwise addition of trifluoroacetic anhydride (7.41 mL, 52.5 mmol). The reaction was stirred for 30 min and then the ice bath was removed. The reaction was then stirred for 3 h and then the bulk of MeCN was removed by rotary evaporation. The residue was dissolved in EtOAc (150 mL) and washed with sodium thiosulfate (aqueous, 0.5 M, 2×100 mL), water (100 mL), brine (100 mL), dried with sodium sulfate and concentrated to a tan solid. The solid thus obtained was dissolved in DCM (150 mL) and MeOH (30 mL). The solid residue was removed by filtration, and the filtrate was concentrated affording 2-chloro-5-(methoxycarbonyl)pyridine 1-oxide as a tan solid.

1. stirringThe reaction was stirred for 30 min
2. customthe ice bath was removed
3. stirringThe reaction was then stirred for 3 h
4. customthe bulk of MeCN was removed by rotary evaporation
5. dissolutionThe residue was dissolved in EtOAc (150 mL)
6. washwashed with sodium thiosulfate (aqueous, 0.5 M, 2×100 mL), water (100 mL), brine (100 mL)
7. dry with materialdried with sodium sulfate
8. concentrationconcentrated to a tan solid
9. customThe solid thus obtained
10. customThe solid residue was removed by filtration
11. concentrationthe filtrate was concentrated

ORDレコード

ord-f82c18889f50443887ea0ec23d4be1c8

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08710043B2