Methanol → 2-Chloro-6-methoxy-3-nitropyridine

HRID 842974Notes

Reaction equation

HRID 842974 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][OH:13]>>[Cl:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([O:13][CH3:12])[N:3]=1.[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:13][CH3:12])[N:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 852392,6-Dichloro-3-nitropyridine

Product 2

HCID 27950292-Chloro-6-methoxy-3-nitropyridineYield 100%HCID 107977036-Chloro-2-methoxy-3-nitropyridine

Procedure

A slurry of 2,6-dichloro-3-nitropyridine (92%, 9.9 g, 47 mmol) and K2 CO3 powder (6.5 g, 47 mmol) in methanol (100 mL) was stirred for a week at RT. The reaction was filtered and concentrated. The residue was partitioned in ethyl acetate and 60% sat. aq. NaHCO3. The organic solution was washed with 60% sat. aq. NaHCO3 (2×), H2O, then sat. aq. NaCl, dried (MgSO4) and concentrated to afford 2-chloro-6-methoxy-5-nitropyridine and 2-chloro-6-methoxy-3-nitropyridine (8.9 g, 100%) as a light yellow solid: 1H NMR (CDCl3, 300 MHz, ppm) 8.31 (d, 8.3 Hz, 1H), 8.28 (d, 8.9 Hz, 1H), 7.10 (d, 8.3 Hz, 1H), 6.82 (d, 8.9 Hz, 1H), 4.15 (s, 3H), 4.06 (s, 3H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe residue was partitioned in ethyl acetate
  4. washThe organic solution was washed with 60% sat. aq. NaHCO3 (2×), H2O
  5. dry with materialsat. aq. NaCl, dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-889b43312fe942c9a6d35328b7beb672
Source dataset
uspto-grants-2002_04
Patent number
US06376538B1

Reaction notes

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