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

HRID 728771

반응식

HRID 728771 반응식
[Na].Cl[C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1.[CH3:13][OH:14]>>[CH3:13][O:14][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1

참가 물질

4

반응물 3

HCID 887Methanol2회HCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 5360545Sodium

생성물 1

HCID 2431692-Methoxy-4-methyl-5-nitropyridine수율 98%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c3e9f5f7b8d415e9fd907ad9528d4a4
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051412

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