反应详情

温度

75 °C

1,1-Dimethylethyl 7-[(hydroxyamino)(imino)methyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 41) (240 mg, 0.785 mmol) was added to a suspension of sodium hydride (60% dispersion in mineral oil) (23.01 mg, 0.575 mmol) in THF (5 ml) at room temperature (note slight effervescence). The resultant mixture was stirred at room temperature for 30 mins, methyl 3-cyano-4-(methyloxy)benzoate (100 mg, 0.523 mmol) was then added and the reaction mixture was heated to reflux (75° C.) for 45 mins. The reaction mixture was diluted with water and ethylacetate and the layers partitioned, solid was present in the bi-phasic mixture so this was transferred to a conical flask and stirred at room temperature for 2 h at room temperature. The mixture was then partitioned and the organic layer concentrated in vacuo. to yield the title compound (280 mg, 0.502 mmol, 96% yield) as a yellow oil. MS (ES): C25H26N4O4 requires 447; no mass ion present. 1H NMR (400 MHz, CDCl3) δ 1H, d (8.44), 1H, dd (8.38), 2H, m (7.89-7.95), 1H, m (7.35-7.42), 1H, m (7.13-7.17), 3H, s (4.06), 4H, m (3.50-3.66), 4H, m (2.87-3.06), 9H, s (1.50).

1. temperaturethe reaction mixture was heated
2. customthe layers partitioned
3. customthis was transferred to a conical flask
4. customThe mixture was then partitioned
5. concentrationthe organic layer concentrated in vacuo