Iodoethane → 4-Sec-butylpyridine

HRID 1764093Notes

Reaction equation

HRID 1764093 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2].[CH2:9](I)[CH3:10]>N>[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)([CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 6340Iodoethane2×HCID 108224-Ethylpyridine

Product 1

HCID 155569384-Sec-butylpyridine

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A method similar to that of Brown and Murphey is employed.4Approximately 500 ml of NH3 was condensed in a 1-liter flask; 1 mole of sodium amine (Fisher) followed by 1.0 mole of 4-ethylpyridine is added to the flask. After stirring under NH3 reflux for 30 minutes, 1.1 mole of ethyl iodide is added via an addition funnel to the orange-red suspension over a 1.5 hour period. Stirring is continued after the ethyliodide addition is complete and the solvent is allowed to evaporate slowly. Water (50 ml) is added to the residue and the layers are separated. The aqueous layer is extracted with ether and the combined organic layers are dried over Na2CO3, concentrated, and distilled. A colorless oil, 117.2 gm (87%), bp 120-25/90mm (lit.5 128°-30°/100 mm) is collected. The oil exhibits an nmr signal typical for a sec-butyl group in addition to the usual pattern for 4-substituted pyridine.

Workup

  1. customcondensed in a 1-liter flask
  2. additionis added to the flask
  3. temperaturereflux for 30 minutes
  4. stirringStirring
  5. customto evaporate slowly
  6. additionWater (50 ml) is added to the residue
  7. customthe layers are separated
  8. extractionThe aqueous layer is extracted with ether
  9. dry with materialthe combined organic layers are dried over Na2CO3
  10. concentrationconcentrated
  11. distillationdistilled
  12. customA colorless oil, 117.2 gm (87%), bp 120-25/90mm (lit.5 128°-30°/100 mm) is collected
  13. additionin addition to the usual pattern for 4-substituted pyridine

Sources & evidence

ORD record
ord-3d80385a5a354f70a44601ec6e3aadc9
Source dataset
uspto-grants-1978_09
Patent number
US04115397

Reaction notes

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