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

HRID 728771

Reaction equation

HRID 728771 reaction equation
[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

Participants

4

Reactant 3

HCID 887Methanol2×HCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 5360545Sodium

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7c3e9f5f7b8d415e9fd907ad9528d4a4
Source dataset
uspto-grants-1991_09
Patent number
US05051412

Linked notes

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