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

HRID 876845Notes

Reaction equation

HRID 876845 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][N+:10]([O-:12])=[O:11])[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 4216172,6-Dichloro-4-nitraminopyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2,6-Dichloropyridin-4-amine (3.0 g, 18 mmol) was carefully added to concentrated sulfuric acid (20 mL). The mixture was cooled in an ice bath, and fuming nitric acid (2.6 mL) was added dropwise via pipette. The mixture was warmed to room temperature and stirred for 1 h, then poured onto crushed ice, resulting in a white precipitate. The white precipitate was collected by filtration, washed with cold water, and dried to afford the title compound (3.7 g), which was used for next step without further purification.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. additionpoured
  3. customonto crushed ice
  4. customresulting in a white precipitate
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-acdc60b1d9304399ad6aec26965d14bb
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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