2-Chloro-3-methyl-5-nitropyridine → 2-Methoxy-3-methyl-5-nitropyridine

HRID 2088506Notes

Reaction equation

HRID 2088506 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 896482-Chloro-3-methyl-5-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 407869042-Methoxy-3-methyl-5-nitropyridineYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Chloro-3-methyl-5-nitropyridine (67.0 g, 0.389 mol) was dissolved in anhydrous methanol (600 ml) and 0.5 M NaOMe in MeOH (800 mL) was added slowly to the mixture (temperature rises to ca. 30° C.). The reaction mixture was stirred at room temperature overnight. The solution was concentrated and the residue was transferred to a separatory funnel containing water (2 L). The aqueous layer was extracted with CH2Cl2 (2×2 L). The combined organic layers were dried over MgSO4, filtered and concentrated to give 2-methoxy-3-methyl-5-nitropyridine (63.0 g, 97% yield) as a white solid which was dried under vacuum: 1H NMR (400 MHz, CDCl3) δ 8.91 (d, J=2.0 Hz, 1H), 8.16 (s, 1H), 4.06 (s, 3H), 2.25 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 165.83, 141.91, 139.37, 132.92, 121.77, 54.83, 15.84; An analytical sample was recrystallized from hexane to give white needles, mp 95-96. 5° C.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was transferred to a separatory funnel
  3. additioncontaining water (2 L)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×2 L)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-67fd0e885eda46359aab5bbdfe7ce7cb
Source dataset
uspto-grants-2013_05
Patent number
US08436000B2

Reaction notes

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