Category: 5398-69-6

Some common heterocyclic compound, 5398-69-6, name is 2-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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. Computed Properties of C7H4INO4

2-Iodo-3-nitro-benzoic Acid Methyl Ester 2-iodo-3-nitro-benzoic acid (61 g, 208 mmol, prepared as described in Org. Syn. Coll. Vol. 1, 56-58, and 125-127), sulfuric acid (40.8 g, 416 mmol), and trimethyl orthoformate (88.4 g, 833 mmol) were dissolved in 500 mL dry MeOH. The reaction was refluxed under argon for 20 h. The reaction mixture was concentrated to 100 mL then partitioned between saturated NaHCO3(aq) and CH2Cl2. The layers were separated and the aqueous layer extrated three times with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The yellow solid was crystallized from CH2Cl2/hexanes yielding 2-iodo-3-nitro-benzoic acid methyl ester, 57.8 g (90%) as a yellow solid: m.p.64.0-64.5 C.; 1H NMR (300 MHz, CDCl3) 3.99 (s, 3H), 7.54 (app t, J=7.8 Hz, 1H), 7.70 (dd, J=8.1, 1.8 Hz, 1H), 7.77 (dd, J=7.8, 1.8 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5398-69-6, its application will become more common.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US6495541; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5398-69-6, A common heterocyclic compound, 5398-69-6, name is 2-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, its 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.

Reference Example 116 methyl 2-iodo-3-nitrobenzoate A mixture of 2-iodo-3-nitrobenzoic acid (31.0 g, 106 mmol) and concentrated sulfuric acid (24.9 mL, 317 mmol) in methanol (600 mL) was heated under reflux for 12 hr. The solvent was evaporated under reduced pressure and the residue was extracted with methylene chloride. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (chloroform /hexane) to give the title compound (31.0 g, yield 95%). 1H-NMR (DMSO-d6) delta: 3.90 (3H, s), 7.70 (1H, t, J = 7.6 Hz), 7.82 (1H, dd, J = 7.6, 1.2 Hz), 7.98 (1H, dd, J = 7.6, 1.2 Hz).

The synthetic route of 5398-69-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2141150; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com