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. Recommanded Product: 61203-48-3
Examples 2.a-6.a[152] The intermediate 4-amino-6,7-methylenedioxycinnoline o-iodobenzamide derivatives used in Examples 2-6 were prepared using the following general procedure. [153] A 2.0M solution of oxalyl chloride in CH2Cl2 (1.3 equiv.) was added to a solution of 2-iodo-4,5-dimethoxybenzoic acid (1.0 equiv.) in anhydrous CH2Cl2 (§ 60 mL per 10 mmol benzoic acid) and the solution stirred at reflux for 3 h. The mixture was allowed to cool and was then concentrated to dryness in vacuo. To the residues was added a solution of requisite 4-amino-6,7-dimethoxyquinoline (1.0 equiv), triethylamine (2 equiv.) in CH2Cl2 (§ 60 mL per 4 mmol aminoquinoline). The reaction mixture was then stirred at reflux under N2. The reaction mixture was cooled and washed with sat. NaHCO3 and extracted with 3% HCl. The aqueous layer was neutralized with 20% NaOH and extracted with CHCl3, dried (MgSO4) and evaporated. [154] Example 2.a. N-(6,7-Methylenedioxycinnolin-4-yl)-N-(N,N-diethylaminoethyl)- 2-iodo-4,5-dimethoxybenzamide: Prepared from N’-(6,7-Methylenedioxycinnolin-4- yl)-N,N-diethylethane-1,2-diamine (640 mg, 2.2 mmol); (87% yield); reaction time 16 h; IR (CHCl3) 1656; 1H NMR (CDCl3) 0.92 (t, 6H, J=7.0), 2.50 (q, 4H, J=7.0), 2.80 (t, 2H, J=6.8), 3.39 (s, 3H), 3.71 (s, 3H), 3.94 (m, 1H), 4.41 (m, 1H), 6.21 (d, 2H, J=1.4), 6.39 (s, 1H), 7.01 (s, 1H), 7.39 (s, 1H), 7.64 (s, 1H), 9.11 (s, 1H); 13C NMR (CDCl3) 11.6, 46.9, 47.8, 51.1, 55.7, 56.1, 82.9, 96.9, 102.9, 105.5, 110.9, 122.1, 122.9, 133.0, 136.5, 144.9, 148.3, 150.1, 150.9, 151.7, 152.3, 169.8; HRMS calcd for C24H27O5N41H: 579.1105; found: 579.1105.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61203-48-3, its application will become more common.
Reference:
Patent; GENZYME CORPORATION; TEICHER, Beverly A.; SCHMID, Steven M.; WO2012/15875; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com