3-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester → N-cyano-N'-(3-nitroxypropyl)-3-pyridinecarboximidamide

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 3-nitroxypropylamine nitrate (0.53 g, 2.9 mmol) and sodium methoxide (0.16 g, 2.9 mmol) were added. The mixture was stirred at room temperature for 18 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue was extracted with chloroform (30 ml×3). The chloroform layer was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with chloroform-methanol (60:1). Eluted fractions were concentrated under reduced pressure and crystallized from methanol-diethyl ether to give the title compound (0.26 g, 1.0 mmol, yield: 39%) as colorless crystals.

1. concentrationthe reaction solution was concentrated under reduced pressure
2. extractionthe residue was extracted with chloroform (30 ml×3)
3. washThe chloroform layer was washed with water (100 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe concentrated residue thus obtained
7. washeluting with chloroform-methanol (60:1)
8. concentrationEluted fractions were concentrated under reduced pressure
9. customcrystallized from methanol-diethyl ether

ORD record

ord-d14fe50d3e4047a8a3e294f045a77354

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166347