2-Amino-3,5-dinitropyridine → 5-Nitropyridine-2,3-diamine

HRID 854072Notes

Reaction equation

HRID 854072 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1>CO>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 5043402-Amino-3,5-dinitropyridine

Product 1

HCID 34801515-Nitropyridine-2,3-diamineYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 2-Amino-3,5-dinitropyridine (2) (1.62 g, 8.8 mmol) in MeOH (75 mL) was added an aqueous solution of (NH4)2S (20%, 15 mL, 44 mmol) dropwise at room temperature over 20 minutes. The mixture was stirred for an additional 30 minutes at room temperature and then heated at reflux for 30 minutes. The solution was cooled to room temperature and the solid collected by filtration, rinsed with cold MeOH (2×20 mL), and dried in vacuo at room temperature to give 3 as a red solid (0.812 g, 5.27 mmol, 60%). 1H NMR (500 MHz, DMSO-d6) δ 5.31 (s, 2H), 6.98 (s, 2H), 7.35 (d, J=2.55 Hz, 1H), 8.28 (d, J=2.91 Hz, 1H). EIMS M+1 155.1.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. temperatureThe solution was cooled to room temperature
  4. filtrationthe solid collected by filtration
  5. washrinsed with cold MeOH (2×20 mL)
  6. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-3e1421e443524c8d9dbb4273cdcee248
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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