Benzoyl Peroxide → [(6-Chloropyridin-2-yl)methyl]dimethylamine

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.Br[N:10]1[C:14](=O)CC[C:11]1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:10]([CH3:14])[CH3:11])[N:3]=1

Participants

Procedure

2-Chloro-6-methylpyridine (6.4 g, 0.05 mol) is refluxed with N-bromosuccinimide (8.9 g, 0.05 mol) in 50 ml of carbon tetrachloride with benzoyl peroxide (50 mg) until the N-bromosuccinimide has reacted completely (7-14 hours). The succinimide is removed by filtering and the filtrate is saturated with anhydrous dimethylamine. Dimethylamine hydrochloride is removed by filtration and the filtrate is concentrated in vacuo. The residual oil is taken up in hexane and extracted into dilute hydrochloric acid. After the acid extract is washed with ether it is made basic with sodium hydroxide and extracted with ether. The ether extract is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 2.2 g of 2-chloro-6-dimethylaminomethylpyridine as a pale yellow oil.