Ethanol → 2-Ethoxy-5-nitropyridine

HRID 276836Notes

Reaction equation

HRID 276836 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-93c19fe993d844d1992b65531fc5e83c
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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