2-Chloro-5-nitropyridine → 2-Tert-butoxy-5-nitropyridine

HRID 46467Notes

Reaction equation

HRID 46467 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1>C(O)(C)(C)C>[C:2]([O:4][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1)([CH3:5])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 146572632-Tert-butoxy-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 50 ml. of tert-butanol, there was added potassium tert-butoxide (0.06 mole) and 2-chloro-5-nitropyridine (0.05 mole). A white solid precipitated. The reaction mixture was heated to about 60° for 4 hours. Excess ammonium chloride was added to neutralize excess potassium tert-butoxide. Solvent was removed by evaporation, and the residue was taken up in chloroform, separated, washed with water, dried over magnesium sulfate, and chromatographed on silica gel with a 50:50 mixture of ethyl acetate:toluene. The structure was confirmed by NMR spectroscopy.

Workup

  1. customA white solid precipitated
  2. temperatureThe reaction mixture was heated to about 60° for 4 hours
  3. additionExcess ammonium chloride was added
  4. customSolvent was removed by evaporation
  5. customseparated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customchromatographed on silica gel with a 50:50 mixture of ethyl acetate

Sources & evidence

ORD record
ord-dd2df57558654f3c918b06d808c909c9
Source dataset
uspto-grants-1979_11
Patent number
US04173639

Reaction notes

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