反应详情

Compound 1a (8.0 g, 38.3 mmol) was stirred in phosphorous oxychloride (20 mL, 218 mmol) at RT. Dimethylaniline (1 mL, 7.9 mmol) was added, and the reaction stirred for 16 h. The solution was concentrated in vacuo, quenched with ice, and made basic with sat. NaHCO3 solution. The aqueous solution was concentrated in vacuo. The residue was taken up in a 20% MeOH/CH2Cl2 and insoluble inorganic salts were removed by filtration. Organics were concentrated and purified by silica gel chromatography (75% EtOAc/CH2Cl2) to give 6.02 g (69%) of compound 1b as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.46 (s, 1H), 3.99 (t, 2H, J=7.6 Hz), 3.78 (s, 3H), 3.30 (t, 2H, J=7.6 Hz), 2.04-2.14 (m, 2H). MS (ES) [m⇄H] calc'd for C10H10ClNO3, 228, 230. found 228, 230.

1. concentrationThe solution was concentrated in vacuo
2. customquenched with ice
3. concentrationThe aqueous solution was concentrated in vacuo
4. customwere removed by filtration
5. concentrationOrganics were concentrated
6. custompurified by silica gel chromatography (75% EtOAc/CH2Cl2)