Nitric Acid → 2-Chloro-4-nitropyridine 1-oxide

HRID 1369197Notes

Reaction equation

HRID 1369197 reaction equation
[N+:1]([O-:4])(O)=[O:2].Cl.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:13].[OH-].[Na+]>OS(O)(=O)=O>[Cl:6][C:7]1[CH:12]=[C:11]([N+:1]([O-:4])=[O:2])[CH:10]=[CH:9][N+:8]=1[O-:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 88478Chloride 2-chloropyridinium 1-oxide

Product 1

HCID 844332-Chloro-4-nitropyridine 1-oxideYield 37%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of conc. H2SO4 (30 mL) and fuming HNO3 (54 mL) was added dropwise at 0° C. to a solution of 2-chloropyridine-N-oxide hydrochloride (15.2 g, 91.56 mmole) in conc. H2SO4 (30 mL). The reaction mixture was heated at 90° C. for 1 hr, then was cooled to RT and poured onto ice (500 g). The reaction mixture was kept at RT overnight, then was cooled in an ice bath, and 50% NaOH was added slowly to give a precipitate. This was collected and dried to give the title compound (5.88 g, 37%) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ8.42-8.37 (m, 2 H), 8.06-8.04 (m, 1 H).

Workup

  1. temperaturewas cooled to RT
  2. additionpoured onto ice (500 g)
  3. temperaturewas cooled in an ice bath
  4. customto give a precipitate
  5. customThis was collected
  6. customdried

Sources & evidence

ORD record
ord-4dca45304f5b4e3eb5b40d6c9ed40b36
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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