Benzoyl chloride → HCID 69673097, compound

Participants

Reaction Steps

2-Phenyl-6,7,8,9-tetrahydro-naphtho[2,3-d][1,3]oxazin-4-one was prepared by a modification of the route described in Okabe, M. and Sun, R. C.; Tetrahedron 1995, 51(7), 1861-1866. A 100 mL flask was charged with 3-amino-5,6,7,8-tetrahydro-napthalene-2-carboxylic acid, prepared in 36% yield as described in WO 2007/081572 (360 mg, 1.88 mmol) and sodium carbonate (399 mg, 3.77 mmol) and was then evacuated and backfilled with dry nitrogen gas twice before the addition of anhydrous tetrahydrofuran (50 mL). Cooled in an ice bath and added benzoyl chloride (662 mg, 4.71 mmol) and allowed to warm to ambient temperature overnight with stirring. Evaporated in vacuo and partitioned between ethyl acetate and water (20 mL each). Organic fraction was separated, dried with a hydrophobic frit, evaporated onto silica gel, and chromatographed using ISCO Companion with a Redisep silica gel 12 g cartridge and a gradient of heptane and ethyl acetate (0% to 50%). Impure fractions were combined and crystallized from refluxing heptane solution (˜100 mL). Pure material from the column was combined with material obtained by crystallization to give 2-phenyl-6,7,8,9-tetrahydro-naphtho[2,3-d][1,3]oxazin-4-one as a white solid 232.3 mg (44.5% Yield) LCMS (5 min acidic) 3.19 min 100% pure by ELSD, 36-100% pure by UV, ES+/AP+ 278. HNMR (CDCl3) >95% Pure 8.31-8.29 (m, 2H), 7.96 (s, 1H), 7.57-7.47 (m, 3H), 7.41 (s, 1H), 2.95-2.92 (m, 4H), 1.89-1.86 (m, 4H).

Provenance & Evidence