反应详情

温度

-78 °C

To a suspension of 2-chloro-8-methylquinoline-3-carboxaldehyde (10 g, 48.6 mmol) in dry THF (100 mL) under nitrogen cooled to −78° C. was added dropwise over 1 h methylmagnesium bromide (40 mL, 121.6 mmol, 3.0M solution in Et2O). The reaction was allowed to warm to r.t. and stirred for a further 1 h before being poured slowly into NH4Cl solution (100 mL). The mixture was extracted with EtOAc (2×200 mL) and the organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as an off-white solid (8.0 g, 74%). δH (CDCl3) 8.33 (s, 1H), 7.68 (d, J 8.0 Hz, 1H), 7.55 (d, J 7.2 Hz, 1H), 7.44 (t, J 7.6 Hz, 1H), 5.34-5.40 (m, 1H), 2.77 (s, 3H), 1.61 (d, J 6.4 Hz, 3H). LCMS (ES+) 222, 224 (M+H)+, RT 3.01 minutes (Method 5).

1. temperatureto warm to r.t.
2. extractionThe mixture was extracted with EtOAc (2×200 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo