These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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. Computed Properties of C8H8INO2
(E)-3-(Naphthalen-2-yl)but-2-enoic acid (1.00 g, 4.71 mmol) was suspended in dry dichloromethane (15 mL) in a flame dried flask under an argon atmosphere and cooled to 0 C. Oxalyl chloride (0.848 g, 0.447 mL, 9.42 mmol) and a catalytic amount of DMF (2 drops) was added to the suspension and allowed to warm to room temperature. The solution was stirred at room temperature for 5 h after which all volatiles were removed under reduced pressure. The crude product was redissolved in dry dichloromethane (15 mL) and solvent removed under reduced pressure three times before drying under high vac. The crude product was redissolved in dry THF (20 mL) in a flame-dried flask under an argon atmosphere. To this was added 5-iodo-2-aminobenzoate (1.86 g, 7.07 mmol), pyridine (1.12 g, 1.14 mL, 14.1 mmol) and a catalytic amount of DMAP (0.01 g, 0.082 mmol). After stirring at 60 C for 16 h, the reaction was allowed to cool to room temperature, poured onto 1 N HCl and extracted into diethyl ether. The combined organic layers were dried over anhydrous magnesium sulphate and concentrated under vacuum to give the crude product.Purification by flash chromatography (8% methanolin dichloromethane) afforded the analytically pure product. (Yield:1.60 g, 3.39 mmol, 72%).1H NMR (CDCl3, 500 MHz, 20 C): delta =11.18(s, 1H, NH), 8.70 (d, J = 9.1 Hz, 1H, ArH), 8.36 (d, J = 2.2 Hz, 1H, ArH),7.98 (d, J = 1.3 Hz, 1H, NpH), 7.89 (m, 3H, ArH NpH), 7.83 (d,J = 2.2 Hz, 1H, NpH), 7.64 (dd, J = 8.5, 1.9 Hz, 1H, NpH), 7.53 (m, 2H,NpH), 6.37 (q, J = 0.9 Hz, 1H, COCH), 3.95 (s, 3H, COOCH3), 2.77 (d,J = 1.0 Hz, 3H, CCH3). 13C NMR (CDCl3, 125 MHz, 20 C): delta =167.6,165.3,154.0,143.1,141.7,139.6,139.3,133.4,133.1,128.5,128.2,127.6,126.6, 126.5, 125.8, 124.0, 122.2, 120.8, 116.5, 84.7, 52.6, 18.0. ESMScalcd for C22H18INNaO3 [M+Na]+: 494.0224, found 494.0221. HPLC(method A): Rt = 14.14 min.
The synthetic route of Methyl 2-amino-5-iodobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Article; Waghorn, Philip A.; Jackson, Mark R.; Gouverneur, Veronique; Vallis, Katherine A.; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 117 – 129;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com