Ethanol → 2-Ethoxy-5-nitropyridine

HRID 1956405Notes

Reaction equation

HRID 1956405 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Na].[CH2:12]([OH:14])[CH3:13]>>[CH2:12]([O:14][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH3:13]

Participants

4

Reactant 3

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

Product 1

HCID 2958642-Ethoxy-5-nitropyridine

Procedure

2-Chloro-5-nitropyridine (30.0 g) was added to a solution of sodium metal (4.4 g) in absolute ethanol (250 ml) under a nitrogen atmosphere. The mixture was boiled under reflux for 4 hours, then cooled slightly and filtered. The filtrate was cooled in ice and filtered to give 2-ethoxy-5-nitropyridine, m.p. 85°-88° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled slightly
  3. filtrationfiltered
  4. temperatureThe filtrate was cooled in ice
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c74d258afec84df7bd3493fb4499787c
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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