Application 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.
[C.] [N- (6-NITROQUINOLIN-4-YL)-N- (N, N-DIMETHYLAMINOETHYL)-2-IODO-5,] 6- dimethoxybenzamide (8c). Oxalyl chloride (1.5 g, 12.0 mmol) was added to a solution of 3, 4-dimethoxy-6-iodobenzoic acid (985 mg, 3.2 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7c (700 mg, 2.7 mmol) and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3 x 75 mL), and extracted with 5 % aqueous HCl (4 x 100 mL). The combined aqueous extracts were basified with 30% [NAOH] and then extracted with chloroform (3 x 100 mL). Combined organic extracts were then dried [(MGSO4)] and evaporated to give 1.15 g of the amide, in 78 % yield ; 1H NMR [(CDC13)] 8 2.23 (s, 6H), 2.63 (m, 2H), 3.35 (s, 3H), 3.71 (s, 3H), 3.96 [(M,] 1H), 4.29 (m, 1H), 6.50 (s, 1H), 6.94 (s, [1H),] 7.79 (d, 1H, [J=5.] 2), 8.22 (d, [1H,] [J=9.] 2), 8. 48 (d, 1H, J=9. 2), 9.0 (d, 1H, J=5. 2), 9.28 (s, [1H)] ; [13C] NMR [(CDC13)] [5] 45.5, 48.0, 55.6, 56.1, 56. 8, 82.3, 110.7, 120.9, 121.5, 122.9, 123.4, 125.5, 132.2, 133.7, 145.9, 148.4, 149.1, 149. 8, 151.5, 154.1, 169.7 ; IR (CHC13) 1345,1535, 1655.
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; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com