2-Chloro-4-nitropyridine → 2-Chloro-4-ethoxypyridine

HRID 1050105Notes

Reaction equation

HRID 1050105 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[O-:11][CH2:12][CH3:13].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 7351522-Chloro-4-nitropyridineHCID 2723922Sodium ethoxide

Product 1

HCID 8172382-Chloro-4-ethoxypyridineYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2-chloro-4-nitropyridine (20 g, 126 mmol) in THF (200 mL) was added sodium ethoxide (25.8 g, 378 mmol) in portions. The mixture was stirred at 25° C. for 10 h. The mixture was filtered and the filtrate was concentrated. The crude material was purified by silica column chromatography (PE/EA=5:1). All fractions found to contain product by TLC (PE/EA=5:1, Rf=0.6) were combined and concentrated to yield a light yellow solid of 2-chloro-4-ethoxypyridine (13 g, 71.9 mmol, 57% yield): 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J=5.2 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 6.73 (dd, J=2.0, 6.0 Hz, 1H), 4.09 (q, J=7.2 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H); ES-LCMS m/z 158 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude material was purified by silica column chromatography (PE/EA=5:1)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-22509e27aca84e62a3ac88be968e158e
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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