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

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16]O)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[K+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[CH2:8][NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][C:4]=2[CH:3]=1

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 14797Potassium Hydroxide

HCID 14260872(2-{[(4-Chlorophenyl)methyl]amino}phenyl)methanol

Product 1

HCID 541749289Chloro-6,11-dihydro-5H-dibenz[b,e]azepineYield 95%

Procedure

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).