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

HRID 53602Notes

Reaction equation

HRID 53602 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 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-chloro-3,5-dinitropyridine (2.035 g, 10 mmol) in EtOH (15 mL) was added aq. NH4OH (6 mL) dropwise at room temperature with stirring over 20 min. The resulting mixture was stirred at room temperature for 15 min, then cooled to 0° C. The precipitate was filtered, washed with water (3×5 mL) and dried to give 1.64 g (89%) of 61 as a yellow powder, mp 190°-1° C. (lit. 190°-2° C., Chemical Abstracts 63:14876 (1965)). 1H NMR (DMSO-d6): 8.697 (bs, 1H, D2O exchange), 8.947 (d, 1H, J=2.5), 9.164 (d, 1H, J=2.5), 9.224 (bs, 1H, D2O exchange).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 15 min
  2. filtrationThe precipitate was filtered
  3. washwashed with water (3×5 mL)
  4. customdried

Sources & evidence

ORD record
ord-49383da603094f25b82474762abd8eab
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

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