Ethanol, 2-amino-, 1-nitrate, nitrate (1:1) → N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboximidamide

HRID 374144

Reaction equation

HRID 374144 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[N+]([O-])(O)=O.[O:19]([CH2:23][CH2:24][NH2:25])[N+:20]([O-:22])=[O:21].C[O-].[Na+]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:25][CH2:24][CH2:23][O:19][N+:20]([O-:22])=[O:21])#[N:2]

Participants

5

Reactant 3

HCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 123958N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboximidamideYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 2-nitroxyethylamine nitrate (0.49 g, 2.9 mmol) and sodium methoxide (0.16 g, 2.9 mmol) were added. The mixture was stirred at room temperature for 10 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue was extracted with dichloromethane (50 ml×3). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was crystallized from dichloromethane-diethyl ether to give the title compound (0.48 g, 2.1 mmol, yield: 79%) as colorless needles.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane (50 ml×3)
  3. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrated residue was crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-272d94d2824a47178d74b1cb6bb1b946
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Linked notes

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