Methyl iodide → 1-(6-Chloropyridin-3-yl)ethan-1-amine

To a stirred solution of N-(2,4,6-trimethylbenzylidene)-2-chloro-5-pyridylmethylamine (10.9 g) in dried tetrahydrofuran (150 ml) cooled to -70° C. under N2 atmosphere was added butyl-lithium (10 w/v % in hexane, 26 ml), causing an immediate intense color to occur. After 30 minutes stirring at the temperature, methyl iodide (5.7 g) was added dropwise, and then the mixture was stirred for three hours without cooling. The solvent was removed under reduced pressure. To the residue, ethanol (50 ml) and 2N-hydrochloric acid (50 ml) were added and heated under reflux for one hour. The cooled solution was poured into water (100 ml) and extracted with methylene chloride (50 ml×2). The aqueous fraction was neutralized with 2N-sodium hydroxide and extracted with methylene chloride (50 ml×2). The extract was dried over sodium sulfate and evaporated to obtain 1-(2-chloro-5-pyridyl)ethylamine (4 g). nD20 1.5440

1. additionwas added dropwise
2. temperaturewithout cooling
3. customThe solvent was removed under reduced pressure
4. additionTo the residue, ethanol (50 ml) and 2N-hydrochloric acid (50 ml) were added
5. temperatureheated
6. temperatureunder reflux for one hour
7. additionThe cooled solution was poured into water (100 ml)
8. extractionextracted with methylene chloride (50 ml×2)
9. extractionextracted with methylene chloride (50 ml×2)
10. dry with materialThe extract was dried over sodium sulfate
11. customevaporated

ORD record

ord-47749195ee5042bebab7772cb95d3b49

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05238949