Chloroform → 5,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

反応式

[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]([NH2:18])=O)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-].[Na+]>C(N(CC)CC)C>[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]#[N:18])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

実験手順

A mixture of 1.19 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboxamide (see Example 10), 12 ml of chloroform, 2.7 ml of 50% sodium hydroxide solution and 50 mg of triethylamine is stirred at room temperature for 1 hour. The reaction mixture is then poured onto ice/water and the whole is extracted with methylene chloride. The extracts are washed with water, dried over anhydrous sodium sulphate and evaporated, and the residue is purified by flash chromatography on silica gel [eluent: n-hexane/ethyl acetate (9:1)]. There is obtained 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, m.p. 118°-121° C.