Nitric Acid → 2,5-Dichloro-4-nitro-1-oxo-1lambda~5~-pyridine

HRID 895572Notes

Reaction equation

HRID 895572 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[N+:10]([O-:13])(O)=[O:11].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N+:16]=1[O-:22]>OS(O)(=O)=O>[Cl:14][C:15]1[CH:20]=[C:19]([N+:10]([O-:13])=[O:11])[C:18]([Cl:21])=[CH:17][N+:16]=1[O-:22]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 113326572,5-Dichloro-pyridine 1-oxide

Product 1

HCID 222840452,5-Dichloro-4-nitro-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At 0° C., 30% oleum (13 mL) is added slowly to fuming HNO3 (22 mL) and the resulting mixture is added slowly to the solution of 2,5-dichloro-pyridine 1-oxide (5.2 g, 31 mmol) in concentrated H2SO4. After addition, the reaction mixture is warmed to room temperature over 1 hr. then heated to 80° C. for 2 hr. After cooling to room temperature, the mixture is poured into ice (120 g) and precipitate is formed gradually. The solid is collected by filtration and washed with water. The product is obtained as yellow solid. 1H NMR (CDC3) δ 8.46 (s, 1H), 8.25 (s, 1H).

Workup

  1. additionAfter addition
  2. temperaturethen heated to 80° C. for 2 hr
  3. temperatureAfter cooling to room temperature
  4. customprecipitate is formed gradually
  5. filtrationThe solid is collected by filtration
  6. washwashed with water
  7. customThe product is obtained as yellow solid

Sources & evidence

ORD record
ord-6dc3d4b992e34ef9a58ce301e53e0713
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

Loading…