反应详情

To a solution/suspension of 2-amino-3-methoxybenzaldehyde (1.8 g, 11.9 mmol) in dry toluene (30 mL) under nitrogen was added acetic acid (0.1 mL) followed by dimethyl malonate (3.4 mL, 29.8 mmol) and piperidine (2.9 mL, 29.8 mmol). The reaction mixture was heated at reflux for 2 h. After cooling to r.t., the mixture was diluted with water (30 mL) and extracted with EtOAc (2×150 mL). The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated in EtOAc/Et2O and the resulting solid was filtered off and dried in vacuo to give the title compound (1.7 g, 61%) as a pale yellow solid. δH (DMSO-d6) 10.65 (br s, 1H), 8.52 (s, 1H), 7.42 (d, J 8.0 Hz, 1H), 7.27 (d, J 8.0 Hz, 1H), 7.21 (t, J 6.0 Hz, 1H), 3.94 (s, 3H), 3.84 (s, 3H). LCMS (ES+) 234 (M+H)+, RT 2.13 minutes (Method 5).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 2 h
3. extractionextracted with EtOAc (2×150 mL)
4. customThe organic layer was separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was triturated in EtOAc/Et2O
9. filtrationthe resulting solid was filtered off
10. customdried in vacuo