Methanol → 2-Chloropyridine-4-carboximidamide

To a suspension of ammonium chloride (10.7 g, 200 mmol) in 250 mL of dry toluene. was added a 2 M solution of Al(CH3)3 (100 mL, 200 mmol) in toluene dropwise under nitrogen at 0° C. The resulting reaction mixture was stirred at rt until no more evolution of gas was observed and then 2-chloropyridine-4-carbonitrile (13.86 g, 100 mmol) was added. The mixture was stirred at 90° C. overnight. It was then cooled down to 0° C. and 300 mL of methanol were added with subsequent stirring for 1 h at rt. After filtration, the solid was washed with methanol for several times, the solution was evaporated to dryness under vacuum. The residue was washed with methanol to give 2-chloropyridine-4-carboximidamide. (18.3 g, 95%). 1HNMR δ (400 MHz, d6-DMSO): 8.70 (dd, J=4.8, 0.4 Hz, 1H), 8.00 (dd, 0.4 Hz, 1H), 7.84 (dd, J=5.2, 1.6 Hz, 1H), 7.80 (m, 1H), 7.53 (t, J=8.1 Hz, 1H); MS (ESI) m/z (M+H)+ 156.

1. customThe resulting reaction mixture
2. stirringThe mixture was stirred at 90° C. overnight
3. temperatureIt was then cooled down to 0° C.
4. stirringwith subsequent stirring for 1 h at rt
5. filtrationAfter filtration
6. washthe solid was washed with methanol for several times
7. customthe solution was evaporated to dryness under vacuum
8. washThe residue was washed with methanol

ORD record

ord-53df2c66b0494094899bb8b87784d618

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969364B2