Reaction #1687632

Reaction equation

charcoal

acetone oxime

nicotinoyl chloride

ether

→

82

4-Methyl-2-(3-pyridyl)-oxazole

Solvents

ammonia

—

ice water

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise under a nitrogen atmosphere
2. 2
   OtherA violent reaction
3. 3
   TemperatureAfter cooling the mixture
4. 4
   Filtrationfiltered
5. 5
   Otherthe ether phase separated
6. 6
   ExtractionThe aqueous phase was extracted with 2×200 ml of ether
7. 7
   Dryingthe combined organic phase dried over magnesium sulphate
8. 8
   OtherRemoval of solvent in vacuo

Procedure

To 10 g (0.140 mol) of acetone oxime cooled to -10° C. neat nicotinoyl chloride (40 g, 0.280 mol) was added dropwise under a nitrogen atmosphere. A violent reaction occured and the mixture became quickly solid. The solid was heated to 120° C. for 3 h. After cooling the mixture was dissolved in ice water and ammonia. After addition of 300 ml of ether the mixture was treated with charcoal, filtered, and the ether phase separated. The aqueous phase was extracted with 2×200 ml of ether, and the combined organic phase dried over magnesium sulphate. Removal of solvent in vacuo gave crude 82 as a red oil. Yield: 3.9 g (0.024 mol, 17%).

Source