Sodium Bicarbonate → 1-(2-Methyl-pyridin-4-yl)-2-phenyl-ethanone

HRID 333761Notes

Reaction equation

HRID 333761 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:18])[CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)C#N)[CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+]>Br>[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:18])[CH2:9][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 574213293-(2-Methyl-pyridin-4-yl)-3-oxo-2-phenyl-propionitrile

Product 1

HCID 574213301-(2-Methyl-pyridin-4-yl)-2-phenyl-ethanoneYield 26%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3-(2-Methyl-pyridin-4-yl)-3-oxo-2-phenyl-propionitrile (1.02 g, 4.3 mmol) was suspended in HBr (48%, 10 mL) and heated to reflux overnight. The mixture was poured onto ice (20 g), was made alkaline (pH=11) by addition of NaHCO3 (satd.), and extracted with ethyl acetate. The combined organic layers were combined and dried (Na2SO4). After evaporation of the solvent, the title compound (233 mg, 26%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50). 1H NMR (300 MHz, DMSO-D6) 8.66 (1H, d), 7.78 (1H, s), 7.69 (1H, d), 7.35-7.24 (5H, m), 4.43 (2H, s), 2.57 (3H, s); MS (m/e)=212.1 [MH+].

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. additionThe mixture was poured onto ice (20 g)
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-16daa9609b9d42e497938c5b3e88896a
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

Loading…