Sodium Hydroxide → 6-(Oxiran-2-yl)nicotinonitrile

HRID 515115Notes

Reaction equation

HRID 515115 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)=[CH2:2].BrN1C(=[O:17])CCC1=O.[OH-].[Na+]>O.CC(O)(C)C>[O:17]1[CH2:2][CH:1]1[C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 190453106-Ethenylpyridine-3-carbonitrile

Product 1

HCID 595686766-(Oxiran-2-yl)nicotinonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 6-ethenylpyridine-3-carbonitrile (0.742 g, 5.70 mmol) in a 2:1 ratio of H2O:t-BuOH (30 mL) was treated with N-bromosuccinimide in portions over 5 minutes (1.07 g, 5.99 mmol) and stirred at 40° C. for 1 hour. After cooling to 5° C., the reaction was basified with drop wise addition of a solution of sodium hydroxide (0.684 g in 5 mL of H2O, 17.1 mmol) and stirred for another 1 hour. The reaction mixture was poured into H2O (10 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with saturated aqueous NaCl (1×30 mL) and dried over MgSO4. Evaporation of the solvent and purification over SiO2 (0-30% EtOAc hexanes as eluent) provided 6-(oxiran-2-yl) pyridine-3-carbonitrile.

Workup

  1. temperatureAfter cooling to 5° C.
  2. stirringstirred for another 1 hour
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with saturated aqueous NaCl (1×30 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent and purification over SiO2 (0-30% EtOAc hexanes as eluent)

Sources & evidence

ORD record
ord-fff32ad58acd434b99a69e923d6246b0
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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