Nitric Acid → 4-Methyl-3,5-dinitropyridin-2-amine

HRID 1588577Notes

Reaction equation

HRID 1588577 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2431662-Amino-4-methyl-3-nitropyridine

Product 1

HCID 50863994-Methyl-3,5-dinitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 2-amino-4-methyl-3-nitropyridine (25.6 g, 167 mmol) in conc. H2SO4 (50 mL) at 0° C. was added HNO3 (7.77 mL, d=1.49) drop-wise over 30 min. The mixture was warmed to r.t. for 1 h then heated to 50° C. for 60 min. The reaction mixture was cooled and poured into 500 g of ice. The resulting precipitate was filtered, washed with 50 mL of H2O, and air dried to give 2-amino-4-methyl-3,5-dinitro-pyridine as a yellow solid.

Workup

  1. temperaturethen heated to 50° C. for 60 min
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with 50 mL of H2O, and air
  5. customdried

Sources & evidence

ORD record
ord-3b08f841fcf9472b83c866b5e60a18cc
Source dataset
uspto-grants-1993_06
Patent number
US05223499

Reaction notes

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