Ammonium Chloride → 6-Chloro-2-methoxy-3-nitropyridine

HRID 1446467Notes

Reaction equation

HRID 1446467 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[N:6]=1.[Cl-].[NH4+]>C1COCC1>[Cl:14][C:7]1[N:6]=[C:5]([O:2][CH3:1])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 852392,6-Dichloro-3-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 107977036-Chloro-2-methoxy-3-nitropyridineYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxide (1.40 g) was gradually added to a THF (50 mL) solution of 2,6-dichloro-3-nitropyridine (5.00 g) over 30 minutes under ice-cooling. Then, the reaction solution was agitated at 0° C. for 1 hour, and agitated at room temperature for further 12 hours. The reaction solution was poured into a saturated ammonium chloride solution (50 mL), and extracted with ethyl acetate. After drying the organic layer over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate 2:1), and 2.90 g (58%) of 6-chloro-2-methoxy-3-nitropyridine was obtained. The physical properties of the compound are as follows.

Workup

  1. temperaturecooling
  2. stirringagitated at room temperature for further 12 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate 2:1)

Sources & evidence

ORD record
ord-27ef60f2ed994081b18eb5a61285e913
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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