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

HRID 639701Notes

Reaction equation

HRID 639701 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-Dichloro-4-amino pyridine (1.58 g) was taken up in sulfuric acid (20 mL) at 0° C. under a nitrogen atmosphere and nitric acid (2.5 mL) added dropwise. After 30 mins, the reaction turned to an orange colour and was poured slowly into ice water. The precipitate was filtered, washed with water and then dissolved in ethyl acetate. The organic solution was then dried over MgSO4, filtered and evaporated in vacuo to give the title compound (1.7 g) as a yellow solid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. dissolutiondissolved in ethyl acetate
  4. dry with materialThe organic solution was then dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a54b88a0b914493879ad9c94557b2a3
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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