Category: 144550-76-5

Synthetic Route of 144550-76-5, These common heterocyclic compound, 144550-76-5, name is Methyl 2-amino-4-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.

c. Methyl 2-amino-6-ethylbenzoate To a stirred mixture of zinc chloride (8.6 g, 63 mM, previously dried at 200 C. for 2 hr under high vacuum) in tetrahydrofuran (105 mL) under a nitrogen atmosphere was added dropwise a solution of ethyl magnesium chloride (63 mM) in diethyl ether (31.5 mL). After the addition was completed, dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (0.107 g, 0.126 mM) was added to the resulting stirred thick white mixture followed by the dropwise addition of methyl 2-amino-4-iodobenzoate (3.5 g, 12.6 mM) in tetrahydrofuran (15 mL). The resulting reaction mixture was stirred at room temperature for 2.5 hr and then poured slowly into water (300 mL). The water mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated. The residue was chromatographed over silical gel (eluant: Hexanes/diethyl ether; 8.5/1.5) to provide the title ester (1.0 g, 43.5%) as a pale yellow oil; MS(CI): 180 (M+H). 250-MHz 1 H NMR (DMSO-d6); 7.04 (t, J=7.8, 1H), 6.53 (d, J=8.2, 1H), 6.42 (d, J=7.1, 1H), 5.55 (s, 2H, exchangeable), 3.80 (s, 3H), 2.59 (q, J=7.5, 1H), 1.08 (t, J=7.5, 3H).

Statistics shows that Methyl 2-amino-4-iodobenzoate is playing an increasingly important role. we look forward to future research findings about 144550-76-5.

Reference:
Patent; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 144550-76-5

13.8 g of methyl 2-amino-4-iodobenzoate are treated with 48 ml of glacial acetic acid and subsequently with 86 ml of concentrated hydrochloric acid. A solution of 3.8 g of sodium nitrite in 15 ml of water is slowly added dropwise to this suspension which is cooled to -5 C., and stirring is continued at this temperature for 30 minutes. This cooled diazonium salt solution is added dropwise at 0 C. to a solution of 20 ml of sulfur dioxide, 60 ml of glacial acetic acid, 10 ml of water and 3.1 g of copper(II) chloride dihydrate, and stirring is continued first for 1 hour at 0 C. and then overnight at room temperature. The reaction mixture is poured into 1 l of ice-water, and the product is filtered off with suction. This gives 12.7 g of bis(2-methoxycarbonyl-5-iodobenzene)disulfide of m.p. 133 C.-135 C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED; BRISTOW, James Timothy; (11 pag.)US2017/121294; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 144550-76-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

C. 4-Iodo-2-(Quinoxaline-5-sulfonylamino)benzoic acid methyl ester. A solution of methyl 2-amino-4-iodobenzoate (1.2 g, 4.4 mmol), quinoxaline-5-sulfonyl chloride (1.2 g, 5.3 mmol), pyridine (1.7 mL, 22 mmol) and DCM (25 mL) was maintained at 23 C. for 24 h. The reaction mixture was diluted with DCM (200 mL) and washed with satd. aq. NaHCO3, then dried and concentrated to a tan solid. This residue was chromatographed (0 to 100% EtOAc/CH2Cl2) to afford the sulfonamide as a light yellow solid (1.6 g, 77%). MS (ESI): calculated for C16H12IN3O4S, 469.0; m/z found, 470 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 11.10 (s, 1H), 9.07 (d, J=1.8 Hz, 1H), 9.01 (d, J=1.8 Hz, 1H), 8.60 (dd, J=7.4, 1.3 Hz, 1H), 8.40 (dd, J=8.5, 1.3 Hz, 1H), 8.04 (dd, J=7.5, 1.0 Hz, 1H), 7.99 (d, J=1.6 Hz, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.37 (dd, J=8.3, 1.6 Hz, 1H), 3.88 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-4-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allison, Brett D.; Hack, Michael D.; Phuong, Victor K.; Rabinowitz, Michael H.; Rosen, Mark D.; US2005/38032; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2-amino-4-iodobenzoate

e. Dimethyl 7-iodo-4-hydroxyquinoline-2,3-dicarboxylate Using a procedure similar to that described in Example 3c. except starting with methyl 2-amino-4-iodobenzoate, the crude title diester was obtained as a green solid (2.6 g, 92%). This material was purified by chromatography over silica gel (eluant: methylene chloride/methanol; 9.5/0.5) to provide the title compound (0.85 g, 30%) as a tan solid, mp 243-244 C.; MS(CI): 388 (M+H). Analysis for C13 H10 INO5: Calculated: C, 40.33; H, 2.60; N, 3.62 Found: C, 40.26; H, 2.77; N, 3.54

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 144550-76-5, The chemical industry reduces the impact on the environment during synthesis 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, I believe this compound will play a more active role in future production and life.

General procedure: (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%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-4-iodobenzoate, other downstream synthetic routes, hurry up and to see.

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