Dimethyl-p-toluidine → 4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

Participants

Reaction Steps

6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-ol (example C.2) (14.7 g, 40.5 mmol) and N,N-dimethyl-p-toluidine (11.7 mL, 81 mmol) were dissolved in toluene (150 mL) and heated under argon to reflux. Then phosphorous oxychloride (4.1 mL, 44.5 mmol) was added and heating at reflux continued for 9.5 h. The thick suspension became gradually a dark solution. The reaction mixture was allowed to cool and then extracted with dichloromethane (not soluble in toluene), cold 1 N HCl (2×), and sat. NaCl (2×). The product was crystallized from heptane/dichloromethane. One obtained 12 g (78%) of white crystals. MS: m/z=381 (M).

Provenance & Evidence