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

HRID 1681282Notes

Reaction equation

HRID 1681282 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, 100 mmol, 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 concentrted to a solid via evaporation under reduced pressure. This solid was placed in water (25 ml), the pH of which was ad]usted 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 relative intensity) 168 (M+, 98), 167 (100), 151 (34), 138 (24), 80 (17).

Workup

  1. customit was concentrted to a solid via evaporation under reduced pressure
  2. extractionthis aqueous mixture was extracted with ethyl acetate (2×25 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ca3a06a1868a4f8abb8ca3c50e774fdc
Source dataset
uspto-grants-1992_12
Patent number
US05169947

Reaction notes

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