Reaction #63471

Reaction equation

2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

triethylene glycol

hydrazine

potassium hydroxide

→

2-(3-pyridylmethyl)-6-(2-methyl-1,3dioxolan-2-yl)naphthalene

Yield 62.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe temperature was then raised to 210° C. for 1 hour
2. 2
   TemperatureThe mixture was cooled
3. 3
   Extractionextracted with methylene chloride
4. 4
   DryingThe organic layer was dried over sodium sulfate
5. 5
   Otherthe solvent removed under reduced pressure
6. 6
   Otherthe residue chromatographed on silica gel

Procedure

A mixture of 270 mg of 2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, 7 ml of triethylene glycol, 1 ml of anhydrous hydrazine and 500 mg of potassium hydroxide were heated at 160° C. for 30 minutes. The temperature was then raised to 210° C. for 1 hour. The mixture was cooled, poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel to give 160 mg of 2-(3-pyridylmethyl)-6-(2-methyl-1,3dioxolan-2-yl)naphthalene as an oil.

Source