Electric Literature of 63920-73-0,Some common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 28. Preparation of 2-[4-(4-hydroxy-butoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one [0261] To a solution of 4-hydroxy-3,5-dimethyl benzaldehyde (5.00 g, 33.3 mmol) in DMF (30 ml_) were added 4-bromo butan-1-ol (6.11 g, 39.9 mmol) and CS2CO3 (16.24 g, 50.0 mmol). The reaction mixture was stirred at room temperature for 48 hours. Water was added and the products were extracted with ethyl acetate (2 * 200 ml_). The combined organic phase was washed with water (100 ml_), brine (100 ml_), and dried over anhydrous Na2SO4. Solvent was removed and the crude compound was purified using the Simpliflash system (40% ethyl acetate in hexane as eluent) to give 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde as a colorless liquid. Yield: 0.66 g (7%).[0262] To a solution of 2-amino-4,6-dimethoxy-benzamide (0.50 g, 2.53 mmol) and 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde (0.66 g, 2.53 mmol) in N,N-dimethyl acetamide (10 ml_), NaHSO3 (0.50 g, 2.79 mmol) and p-TSA (96 mg, 0.50 mmol) were added and the reaction mixture was heated at 115C for 16 hours, then cooled to room temperature. Solvent was removed under reduced pressure. Water (100 ml_) was added and the mixture was stirred for 1 hour. The solid separated was filtered and dried. The solid was again washed with diethyl ether to give the title compound as a white solid. Yield: 1.69 g (82%). 1H NMR (400 MHz, CDCI3): delta 9.10 (s, 1H), 7.66 (s, 2H), 6.83 (d, J = 2.4 Hz, 1 H), 6.46 (d, J = 2.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.85 (t, J = 6.0 Hz, 2H), 3.78 (m, 2H), 2.36 (s, 6H), 1.94 (m, 2H), 1.85 (m, 2H). MS (ES) m/z: 399.12 (M+1) (100%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,6-dimethoxybenzamide, its application will become more common.
Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
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