Nitric Acid → 2,6-Dichloro-4-nitraminopyridine

HRID 81202

Reaction equation

HRID 81202 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.OS(O)(=O)=O.[N+:15]([O-])([OH:17])=[O:16]>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][N+:15]([O-:17])=[O:16])[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1376524-Amino-2,6-dichloropyridine

Product 1

HCID 4216172,6-Dichloro-4-nitraminopyridine

Conditions

Temperature
0 °C

Procedure

2,6-dichloropyridin-4-amine (100 g, 0.617 mol) was added slowly to conc. H2SO4 (415 mL) by portion while cooled with an ice bath. The mixture was cooled to 0° C., and nitric acid (250 mL) was added dropwise at 0° C. The mixture was stirred at room temperature for 2 h. TLC (petroleum ether/ethyl acetate=2:1) showed the reaction was complete. The mixture was poured into crushed ice and stirred for 30 min. The resulting precipitate was collected by filtration and washed with water to give crude N-(2,6-dichloropyridin-4-yl)nitramide as a yellow solid, which was used for the next step without further purification.

Workup

  1. temperaturewhile cooled with an ice bath
  2. additionThe mixture was poured
  3. custominto crushed ice
  4. stirringstirred for 30 min
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-05adcfb6810f41fbbbef635f537c4b81
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Linked notes

Loading…