Sulfuric Acid → 9Chloro-6,11-dihydro-5H-dibenz[b,e]azepine

Participants

Reaction Steps

2-[[(4-chlorophenyl)methyl]amino]benzenemethanol (6.7 g) (prepared as described in J. Chem. Soc. Chem. Commun., 1989 (1), 44-5) was cooled under a N2 atmosphere to -40° C. Sulfuric acid (35 ml) was added dropwise keeping the temperature at about -10° C. and the mixture was stirred at room temperature for 1 hour. The mixture was poured into ice water and basified carefully with KOH. The mixture was filtered off and the precipitate was washed with water and CH2Cl2. The filtrate and the washings were extracted, dried with Na2SO4, filtered off and evaporated, yielding 5.8 g (95%) of 9-chloro-6,11-dihydro-5H-dibenz-[b,e]azepine (interm. 27).

Provenance & Evidence