8-hydroxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one synthesis

Yield:22246-84-0 76%

Reaction Conditions:

with boron tribromide in 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;

Steps:

33 8-Hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one

Example 33 8-Hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one To a solution of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (1.00 g, 5.23 mmol) in DCM (5 mL) was added dropwise 1M solution of BBr₃ in DCM (5.23 mL). After stirring at room temperature for 30 min, the reaction mixture was heated at reflux for 5 hrs, allowed to cool to ambient temperature and poured into ice-water. The aqueous layer was extracted with DCM (5*10 mL), dried over Na₂SO₄, filtered and evaporated. The solid residue was washed with n-hexane and dried in high vacuum. The title compound was obtained as a white powder (705 mg, 76%). M.P.: 226-227° C.; MS (FAB): calcd for C₁₀H₁₁NO₂ 177.2; found m/e 178 (M+1)⁺. This product was also analyzed by ¹H and ¹³C NMR. The corresponding NMR spectra were consistent with the structure of the anticipated product.

References:

US6514965,2003,B1