Related Products of 61203-48-3,Some common heterocyclic compound, 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, molecular formula is C9H9IO4, 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.
[153] The intermediate 4-N-(2-Dimethylaminoethyl)-N-(2-bromo-4,5- dimethoxybenzoyl)amine-6,7-methylenedioxycinnoline (D) was prepared as follows:[ 154] a. 4-N-(2-Dimethylaminoethyl)-N-(2-bromo-4,5-dimethoxybenzoyl)amine-6,7-methylenedioxycinnoline (D). A 2.0M solution of oxalyl chloride in methylene chloride (5 mL, 10.0 mmol) was added to a solution of 2-iodo-4,5-dimethoxybenzoic acid (1.50g, 4.8mmol) in anhydrous methylene chloride (45 mL) and the stirred mixture was refiuxed for 2 hours. The mixture was then concentrated to dryness under reduced pressure. To this residue was added a solution of N-(2- Dimethylaminoethyl)-4-amino-6,7-methylenedioxycinnoline (3, 1.0 g, 3.84 mmol), and triethylamine (760 mg 7.52 mmol) in methylene chloride (60 mL) and the resulting mixture was stirred at reflux under nitrogen for 4 hours, then cooled to room temperature; stirring was continued overnight. The reaction mix was washed with a saturated solution of sodium bicarbonate (3 x 40 mL), dried (anhydrous MgS04), and concentrated in vacuo. The crude material was chromatographed over silica using 90: 10 chloroform:methanol to give compound D (1.59 g), in 75 % yield; 1H NMR (CDCI3) delta 2.27(s, 6H), 2.53(m, 2H), 3.43(s, 3H), 3.75(s, 3H), 3.97(m, 1H), 4.44(m, 1H), 6.24(s, 1H), 6.25(s, 1H), 6.43(s, 1H), 7.02(s, 1H), 7.43(s, 1H), 7.68(s, 1H), 9.18(s, 1H); 13C NMR (CDC13) delta 45.5, 47.1, 55.7, 56.1, 56.7, 82.8, 96.7, 102.9, 105.4, 110.6, 121.9, 123.2, 133.1, 136.0, 144.8, 148.2, 149.9, 150.9, 151.7, 152.4, 169.8; HRMS calcd for C22H2305N4IH: 551.0791; found 551.0795.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-4,5-dimethoxybenzoic acid, its application will become more common.
Reference:
Patent; GENZYME CORPORATION; TEICHER, Beverly, A.; SCHMID, Steven, M.; WO2012/15901; (2012); A1;,
Iodide – Wikipedia,
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