Sodium Bicarbonate → 2-Phenylindolizine

HRID 450027Notes

Reaction equation

HRID 450027 reaction equation
C(=O)([O-])O.[Na+].[Br-].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=1[CH2:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:16]1([C:15]2[CH:7]=[C:8]3[N:9]([CH:14]=2)[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 123168242-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide

Product 1

HCID 961282-PhenylindolizineYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydrogen carbonate (10.5 g, 119.8 mmol) in water (125 ml) was added to 2-methyl-1-(2-oxo-2-phenyl-ethyl)-pyridinium bromide (35.0 g, 119.8 mmol) and the reaction heated to reflux for 30 min. The resultant solid was filtered, washed with water and then dried under vacuum to yield 2-phenyl-indolizine (16.0 g, 70%).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 30 min
  3. filtrationThe resultant solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e0d62e0532ef4a87b0dfe39f58daa357
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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