Methanol → 2-Methoxy-4-methyl-5-nitropyridine

To a stirred solution of sodium (2.30 g, 100mmol, 3.8 eq) in absolute methanol (75 ml) at 0° C., a solution of 2-chloro-4-methyl-5-nitropyridine (4.50 g, 26.07 mmol) in absolute methanol (15 ml) was added dropwise rapidly. The resulting dark colored solution was stirred at room temperature for 30 minutes, and then it was concentrated to a solid via evaporation under reduced pressure. This solidwas placed in water (25 ml), the pH of which was adjusted to 6 with concentrated HCl, and this aqueous mixture was extracted with ethyl acetate (2×25 ml). These extracts were combined, dried (MgSO4),and evaporated under reduced pressure to yield 2-methoxy-4-methyl-5-nitropyridine (4.30 g, 25.57 mmol, 98%) as an orange solid: mp, 70°-72° C.; 1H NMR (DMSO-d6) δ 8.94 (s, 1H), 6.97 (s, 1H), 3.99 (s, 3H), 2.58 (s, 3H); LRMS (m/z relativeintensity) 168 (M+, 98), 167 (100), 151 (34), 138 (24), 80 (17).

1. concentrationit was concentrated to a solid via evaporation under reduced pressure
2. extractionthis aqueous mixture was extracted with ethyl acetate (2×25 ml)
3. customdried (MgSO4),and evaporated under reduced pressure

ORDレコード

ord-7c3e9f5f7b8d415e9fd907ad9528d4a4

出典データセット

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05051412