反应详情

A suspension of 3H-pyrimido[4,5-b]indol-4(9H)-one (0.091 g, 0.491 mmol) in phosphorous oxychloride (8 mL) was refluxed under nitrogen for 24 hours. Phosphorous oxychloride was removed by evaporation and the residue was partitioned between water (20 mL) and chloroform (2×20 mL). The organic extracts were filtered through celite, dried (Na2SO4) and concentrated to give 4-chloro-9H-pyrimido[4,5-b]indole as a yellow solid (0.103 g, 0.50 mmol, quantitative). 1H NMR (500 MHz, CDCl3) δ 7.60 (1H, dd, J=8.8 Hz), 7.70 (1H, dd, J=8.8 Hz), 8.43 (1H, d, J=8 Hz), 8.52 (1H, d, J=8 Hz), 8.98 (1H, s); LC-MS (3) Rt: 5.59 min; m/z (ESI) 206, 204 [MH+].

1. temperaturewas refluxed under nitrogen for 24 hours
2. customPhosphorous oxychloride was removed by evaporation
3. customthe residue was partitioned between water (20 mL) and chloroform (2×20 mL)
4. filtrationThe organic extracts were filtered through celite
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated