Sodium Hydroxide → HCID 68680258, compound

Participants

Reaction Steps

To a mixture of 8-chloro-5-hydroxyimino-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (3.33 g, 11.2 mmole) and MoO3 (2.45 g, 17.0 μmmole) in MeOH (50.0 ml) was added a solution of sodium borohydride (2.13 g, 56.2 mmole) in DMF (50.0 ml). The reaction was stirred at room temperature overnight. To the reaction mixture was added 2.0N NaOH (aq) (100 ml). The precipitate was removed by filtration, and the filtrate was extracted with ethyl acetate (5×100 ml). The combined organics was washed with brine (3×500 ml). Dried over Na2SO4, filtered and concentrated to 100 ml, which was then treated with 4.0N HCl in dioxane (3.50 ml). Removal of solvents in vacuo gave a white solid, which washed with ethyl ether and dried under vacuum to provide the titled compound as hydrochloride salt (2.87 g, 80%). MS (ES+): 283 (M+H).

Provenance & Evidence