Nitrogen → 3-Chloro-4-methoxybenzylamine hydrochloride

Chlorine gas was bubbled into 400 mL glacial acetic acid with stirring until the weight gained equaled 7% of the starting acetic acid. In a 2 L round bottom flask, 4-methoxybenzylamine hydrogen chloride (32.0 g, 0.18 mol) was suspended in 400 mL glacial acetic acid with vigorous stirring. The chlorine solution (1.5 eq Cl2) was added in rapid drops in 30 min at room temperature. The resulted suspension was stirred for another 20 min before N2 was bubbled in to remove Cl2 and HCl into a 6 N NaOH trap. The acetic acid was evaporated under reduced pressure to 100 mL. To this white slurry, diethyl ether (300 mL) was used to loosen the solid which was then filtered. The solid was resuspended with 50 mL acetic acid followed by the addition of 50 mL diethyl ether and filtration. This process was repeated twice. The white solid was transferred to a 1 L Erhlenmeyer flask and suspended in 400 mL THF. This suspension was heated to boiling for 10 min before filtration. The undissolved solid was filtered, and twice resuspended in boiling THF (100 mL) with filtration to afford the title compound (27.0 g, 71%) as a white solid. This material contained <2% starting material and <2% dichlorinated material.

1. customChlorine gas was bubbled into 400 mL glacial acetic acid
2. customwas bubbled in
3. customto remove Cl2 and HCl into a 6 N NaOH trap
4. customThe acetic acid was evaporated under reduced pressure to 100 mL
5. filtrationwas then filtered
6. additionfollowed by the addition of 50 mL diethyl ether and filtration
7. temperatureThis suspension was heated
8. filtrationto boiling for 10 min before filtration
9. filtrationThe undissolved solid was filtered
10. filtrationwith filtration

ORD record

ord-813929ee992e414aa0280d037db45c38

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06326379B1