Ethanol → 2-Ethoxy-5-nitropyridine

HRID 1266263Notes

Reaction equation

HRID 1266263 reaction equation
[Na].Cl[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][N:4]=1.[CH2:12]([OH:14])[CH3:13]>>[CH2:12]([O:14][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][N:4]=1)[CH3:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 783082-Chloro-5-nitropyridineHCID 5360545Sodium

Product 1

HCID 2958642-Ethoxy-5-nitropyridine

Procedure

To anhydrous ethanol (250 ml) were added sodium (2.25 g, 97.8 mmol) then 2-chloro-5-nitropyridine (15 g, 9.46 mmol) under argon. The resulting mixture was heated at reflux for 10 hrs. After cooling slightly, the mixture was filtered to remove undissolved particles. The filtrate was condensed by rotary evaporation. The residue was triturated with abs ethanol (50 ml). The solid was collected by filtration and dried giving 13.5 g of the product: mp 90-92° C. mass spectrum (electrospray, m/e): 169 (M+H); IR cm-1: 1600, 1508, 1378, 1290, 1118, 1027; H-NMR δ (CDCl3) 1.431 (3H, t, CH3), 4.512 (2H, q, CH2), 6.800 (1H, d, C3-H), 8.337 (1H, dd, C4-H), 9.068 (1H, d, C5-H). See: Friedman et. al., J. Amer. Che. Soc., 69, 1947, 1204.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 10 hrs
  3. temperatureAfter cooling slightly
  4. filtrationthe mixture was filtered
  5. customto remove undissolved particles
  6. customcondensed
  7. customby rotary evaporation
  8. customThe residue was triturated with abs ethanol (50 ml)
  9. filtrationThe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-44a544f8a0ad4e139c997ef4c07c6012
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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