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

HRID 343788Notes

Reaction equation

HRID 343788 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-8571b12bf83442d4a91579a3e96a09c5
Source dataset
uspto-grants-1999_01
Patent number
US05863916

Reaction notes

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