8-nitro-2,3,4,5-tetrahydro-1H-benzo[c]azepine synthesis

Yield:223915-75-1 84%

Reaction Conditions:

Stage #1: 8-nitro-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-onewith borane in tetrahydrofuran; for 4 h;Heating / reflux;
Stage #2: with hydrogenchloride;water in tetrahydrofuran at 0; for 1 h;Heating / reflux;

Steps:

34.iii

8-Nitro-2,3,4,5-tetrahydro-lH-2-benzazepin-l-one (330 mg, 1.60 mmol) was suspended in TΗF (2 ml) and borane (IM in TΗF, 6.5 ml, 6.5 mmol) was added. The mixture was refluxed for 4 h, cooled to O⁰C and hydrochloric acid (4 M, 3 ml) was added carefully. The mixture was refluxed for 1 h, the solvents were evaporated and water (11 ml) was added. The mixture was neutralized by addition of solid sodium hydrogen carbonate. The mixture was extracted with EtOAc (x3). The organic phase was dried (MgSO₄) and the solvent was evaporated. The residue was purified by column chromatography on silica eluting with 10% methanol in chloroform containg 0.1 % triethylamine to give the title compound (258 mg, 84%). MS ESI m/z M+Η⁺ 193.

References:

WO2007/4959,2007,A1 Location in patent:Page/Page column 50