Potassium Carbonate → 2-Chloro-6-methoxy-3-nitropyridine

HRID 1978814Notes

Reaction equation

HRID 1978814 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.[C:12]([O-:15])([O-])=[O:13].[K+].[K+]>CO>[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:15][CH3:12])[N:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 852392,6-Dichloro-3-nitropyridine

Product 2

HCID 27950292-Chloro-6-methoxy-3-nitropyridineYield 200.8%HCID 107977036-Chloro-2-methoxy-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of 2,6-dichloro-3-nitropyridine (92%, 9.9 g, 47 mmol) and K2CO3 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-59239260c5134c7abd77f4e518b4dc09
Source dataset
uspto-grants-2001_05
Patent number
US06239108B1

Reaction notes

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