Nitric Acid → HCID 22176515, compound

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[N+:7]=1[O-:14].OS(O)(=O)=O.[OH-].[Na+]>>[Br:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[CH:9]=[C:8]([CH2:12][CH3:13])[N+:7]=1[O-:14]

Participants

Reactant 4

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 14798Sodium Hydroxide

HCID 221764442-Bromo-6-ethyl-pyridine 1-oxide

Product 1

HCID 22176515HCID 22176515, compoundYield 65%

Conditions

Temperature: 90 °C

Procedure

With ice bath cooling HNO3 (100%, 25 ml) was added dropwise to 2-bromo-6-ethyl-pyridine 1-oxide (example 5a) (20.0 g, 99 mmol), followed by H2SO4 (98%, 17 ml). The mixture was stirred at 90° C. for 90 min and then cooled to rt. Crushed ice (500 g) was added and the pH was adjusted to pH 12 with 28% aqueous NaOH solution. After extraction with AcOEt (4×250 ml) the combined organic phases were dried (Na2CO3) and evaporated to give 15.9 g (65%) of a yellow solid mass which was directly used in the next step