Hydrochloric Acid → HCID 10058859, compound

Into a solution of 3-cyano-5-ethylaminopyridine (380 mg, 2.59 mmol) in 1-propanol (40 ml) was passed hydrogen chloride gas under ice-cooling for 30 minutes. The reactor was tight sealed, and the mixture was stirred at room temperature for 20 hours and concentrated under reduced pressure. After the residue was neutralized with a saturated aqueous sodium carbonate solution and extracted with chloroform (50 ml×3). The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product of propyl 5-ethylamino-3-pyridinecarboximidate. The crude product was then dissolved in acetonitrile (5 ml) and an aqueous solution (18 ml) of cyanamide (210 mg, 5.0 mmol), Na2HPO4 (355 mg, 2.5 mmol) and NaH2PO4 ·2H2O (1.56 g, 10 mmol) was added to the solution, and the mixture was stirred at room temperature over night. After the reaction was completed, the reaction mixture was extracted with chloroform (30 ml×3), and the chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with hexane/ethyl acetate) to give propyl N-cyano-5-ethylamino-3-pyridinecarboximidate (322 mg, 1.38 mmol) as a colorless oil (Yield 54%).

1. temperaturecooling for 30 minutes
2. concentrationconcentrated under reduced pressure
3. extractionextracted with chloroform (50 ml×3)
4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-3f35cdb80f8243ed9970c261c2983a4d

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05508293