Ethanol → 5-Bromo-2-ethoxy-3-nitropyridine

HRID 1695756Notes

Reaction equation

HRID 1695756 reaction equation
[Na].[Br:2][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6](Cl)=[N:7][CH:8]=1.[CH2:13]([OH:15])[CH3:14]>>[Br:2][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([O:15][CH2:13][CH3:14])=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 5360545SodiumHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 582557825-Bromo-2-ethoxy-3-nitropyridine

Procedure

Sodium (3.22 g) was dissolved in absolute ethanol (100 ml) and added dropwise to a suspension of 5-bromo-2-chloro-3-nitropyridine (30.2 g) in ethanol (100 ml) at 0° C. over 10 mins. The cold bath was removed and the reaction stirred at RT for 18 h. The reaction was evaporated to approximately half its volume then diluted with saturated ammonium chloride (aq) (600 ml). The reaction was stirred at RT overnight then the solids were filtered and rinsed well with water. The solids were dissolved in hot ethanol (100 ml) then diluted with hot water (500 ml) and stirred with cooling to RT for 2 hr. The solids were collected and rinsed well with water then suction dried and vacuum dried to give the title compound (26.4 g) as a dark brown solid.

Workup

  1. customThe cold bath was removed
  2. customThe reaction was evaporated to approximately half its volume
  3. additionthen diluted with saturated ammonium chloride (aq) (600 ml)
  4. stirringThe reaction was stirred at RT overnight
  5. filtrationthe solids were filtered
  6. washrinsed well with water
  7. dissolutionThe solids were dissolved in hot ethanol (100 ml)
  8. additionthen diluted with hot water (500 ml)
  9. stirringstirred
  10. temperaturewith cooling to RT for 2 hr
  11. customThe solids were collected
  12. washrinsed well with water
  13. customsuction dried
  14. customvacuum dried

Sources & evidence

ORD record
ord-0e50e6c0e24f4fc4b02391c12120e01f
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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