Allylamine → HCID 77230200, compound

This was prepared by a modification of the method of Schmid, S., et al, Synthesis (2005), (18), 3107-3118. A solution of 2,6-dichloro-3-nitropyridine (8.0 g, 41.45 mmol) in anhydrous dichloromethane (180 ml) was cooled to −15° C., under argon. Triethylamine (6.0 ml, 43 mmol) was added and then allylamine (3.23 ml, 43 mmol) was added in small portions over 3 hours, keeping the temperature at −15° C. The reaction mixture was stirred overnight during which time it warmed to room temperature. The reaction mixture was washed with 0.2M aqueous citric acid (100 ml), saturated aqueous NaHCO3 solution (100 ml), passed through a hydrophobic frit and evaporated to a yellow oil which was purified by chromatography on silica eluting with a 0 to 50% ethyl acetate in hexane giving a yellow solid (7.49 g, 85%).

1. customThis was prepared by a modification of the method of Schmid, S
2. custom, et al, Synthesis (2005), (18), 3107-3118
3. customat −15° C
4. washThe reaction mixture was washed with 0.2M aqueous citric acid (100 ml), saturated aqueous NaHCO3 solution (100 ml)
5. customevaporated to a yellow oil which
6. customwas purified by chromatography on silica eluting with a 0 to 50% ethyl acetate in hexane giving a yellow solid (7.49 g, 85%)

ORD record

ord-b235eeae3bb541d1a6eae3289f087083

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389524B2