Ammonium Hydroxide → 2-Amino-3,5-dinitropyridine

HRID 854074Notes

Reaction equation

HRID 854074 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[NH4+:14].[OH-]>CCO>[NH2:14][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 757382-Chloro-3,5-dinitropyridine

Product 1

HCID 5043402-Amino-3,5-dinitropyridineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro3,5-dinitropyridine (5.38, 26.4 mmol) was suspended in EtOH (75 mL) and NH4OH (28% aq., 30 mL) was added dropwise over 25 minutes with stirring at room temperature. The mixture was stirred for an additional 20 minutes at room temperature and then cooled to 0° C. in an ice bath. The resulting yellow solid was collected by filtration and dried in vacuo at 80° C. to yield 4.42 g (26 mmol, 98%) of yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.69 (br s, 1H), 8.96 (d, J=2.83 Hz, 1H), 9.17 (d, J=2.06 Hz, 1H), 9.26 (br s, 1H). EIMS M+1 185.6.

Workup

  1. stirringThe mixture was stirred for an additional 20 minutes at room temperature
  2. temperaturecooled to 0° C. in an ice bath
  3. filtrationThe resulting yellow solid was collected by filtration
  4. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-f55e3a2404494fd98f26fc615047cdeb
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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