Nitric Acid → 2-Amino-3,5-dinitro-6-methylpyridine

HRID 1588580Notes

Reaction equation

HRID 1588580 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.NC1C=CC([N+:19]([O-:21])=[O:20])=C(C)N=1.[N+]([O-])(O)=O>OS(O)(=O)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:19]([O-:21])=[O:20])=[C:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 2260282-Amino-6-methyl-3-nitropyridineHCID 2479766-Methyl-5-nitropyridin-2-amine

Product 1

HCID 2853032-Amino-3,5-dinitro-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

8.5 g of this mixture of 2-amino-6-methyl-3-nitropyridine and 2-amino-6-methyl-5-nitropyridine was dissolved in H2SO4 (100 mL) at 0° C. and HNO3 (2.74 mL, d=1.49) was added drop-wise over 10 min. After complete addition, the mixture was warmed to 50° C. for 90 min., cooled, then poured onto 200 g of ice. The residue was collected by filtration and washed with cold H2O (2×50 mL) to give 2-amino-6-methyl-3,5-dinitropyridine as a yellow solid.

Workup

  1. additionAfter complete addition
  2. temperaturecooled
  3. filtrationThe residue was collected by filtration
  4. washwashed with cold H2O (2×50 mL)

Sources & evidence

ORD record
ord-0833b0116ef24bbb81c815bcf8238aaa
Source dataset
uspto-grants-1993_06
Patent number
US05223499

Reaction notes

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