Toluene → 8,9,10,11-tetrahydroazepino[1,2-b]isoquinolin-5(7H)-one

Reaction equation

[C:1]1(=O)[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[NH2:13]OC1CCCCCC=1.[C:22]1(C)C=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[CH:11]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[CH:2]=[C:1]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:13]1[C:5]2=[O:7]

Participants

Procedure

Homophthalic anhydride (4.86 g, 30 mmol) was added portionwise over 10 minutes to a refluxing solution of 1-aza-2-methoxycycloheptene (4.20 g, 33 mmol) in toluene. After addition was complete, the reaction mixture was heated an additional 1 h before cooling to ambient temperature. The reaction mixture was diluted with chloroform, the resulting solution was washed twice with sodium hydroxide, and the dried (magnesium sulfate) organic layer was concentrated in vacuo. The residue was chromatographed on silica gel using chloroform, followed by 4% methanol in chloroform, as eluent to give the desired compound. This was triturated with 20% ether in hexanes (40 ml) to yield the title compound as an off-white solid (2.21 g, 42%), m.p. 99-101° C.