Reaction #465969

Reaction equation

sodium bicarbonate

oleum

Methyl 3,6-dichloropyridine-2-carboxylate N-oxide

HNO3

→

yellow solid

4-Nitro-3,6-dichloropyridine-2-carboxylic Acid

Solvents

ethyl acetate

H2SO4

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled in an ice/water bath and to it
2. 2
   OtherThe cooled reaction mixture
3. 3
   ExtractionThe product was extracted with ethyl acetate (2×150 mL)
4. 4
   Dryingthe combined extracts were dried (MgSO4)
5. 5
   Concentrationconcentrated

Procedure

Methyl 3,6-dichloropyridine-2-carboxylate N-oxide (5.0 g, 22.52 mmol) was dissolved in a minimum amount of H2SO4. The mixture was cooled in an ice/water bath and to it was slowly added 30% oleum (9.6 mL) and fuming HNO3 (9.6 mL), gradually heated to 65° C. and stirred for 48 hr. The cooled reaction mixture was diluted with ethyl acetate (200 mL) and to it was carefully added saturated sodium bicarbonate. The product was extracted with ethyl acetate (2×150 mL) and the combined extracts were dried (MgSO4) and concentrated to give 0.10 g of a yellow solid; mp 192-193° C.

Source