Nitric Acid → HCID 22176515, compound

HRID 2307268Notes

Reaction equation

HRID 2307268 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

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22176444HCID 22176444, compound

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

Workup

  1. temperaturecooled to rt
  2. extractionAfter extraction with AcOEt (4×250 ml) the combined organic phases
  3. dry with materialwere dried (Na2CO3)
  4. customevaporated

Sources & evidence

ORD record
ord-0b685dbc2f9e49c0b3919cd78dd0d0b4
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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