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

HRID 57515

Reaction equation

HRID 57515 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

Conditions

Temperature
-5 °C

Procedure

2,6-dichloropyridine-4-ylamine (10.0 g, 61 mmol) was slowly added in concentrated sulfuric acid (64 mL) at the rate to keep the internal reaction temperature <10° C. The mixture was then cooled to −5° C. and nitric acid (90%, 30 mL) was added dropwise to keep the reaction temperature below 0° C. over a period of 40 minutes. The reaction mixture was stirred at 0° C. for 2 hours and then poured into ice-water (500 mL). The title compound was isolated by filtration and dried in vacuo for the next step.

Workup

  1. customthe internal reaction temperature <10° C
  2. customthe reaction temperature below 0° C.
  3. customof 40 minutes

Sources & evidence

ORD record
ord-dd246b41c86a40e2bcd278fecf4bee3a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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