Category: 16017-69-9

Adding a certain compound to certain chemical reactions, such as: 16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16017-69-9, name: Ethyl 4-amino-2-chlorobenzoate

The indicated chloro-aniline (1.02 g, 5.125 mmol) in methanol (13.0 mL) was treated with iodine monochloride (1.0 M in dichloromethane, 5.125 ml, 5.125 mmol) and the solution stirred for 1 hour at room temperature. The reaction mixture was poured into water, followed by aqueous/ethyl acetate work- up, and silica gel chromatography (ethyl acetate : hexanes (2:8) 3.0 % TEA) to give the titled compound.

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Reference:
Patent; MERCK & CO., INC.; WO2007/81335; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 4-amino-2-chlorobenzoate

To a solution of compound 3 (3.02g, 15.1mmol, 1equiv) in anhydrous ethanol (150mL) at 0C were added silver sulfate (4.68g, 15.1mmol) and iodine (3.81g, 15.1mmol). The solution was stirred for 45minat 0C and additional 90minat room temperature. After completion, a saturated aqueous sodium thiosulfate solution was added. The reaction mixture was filtered through Celite, washed with ethanol and filtrate was concentrated to dryness. Water was added and the product was extracted with EtOAc, the combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was triturated with cyclohexane and pentane yielding the compound 4 (3.18g, 9.77mmol, 65%) as a brown powder. Rf=0.3 (EtOAc/cyclohexane 1:9). Mp 125-127C; IR (ATR): 3470-3325, 1702, 1573, 1242cm-1; 1H NMR (400MHz, DMSO-d6): 1.27 (3H, t, J=6.8Hz), 4.21 (2H, q, J=6.8Hz), 6.23 (2H, br s), 6.78 (1H, s), 8.08 (1H, s); 13C NMR (100MHz, DMSO-d6): 14.1 (CH3), 60.4 (CH2), 122.9, 142.2 (CHarom), 114.3, 116.5, 134.3, 153.1 (Carom), 163.0 (CO); HRMS (ESI+) calcd for C9H10ClINO2 (M+H)+ 325.9445, found 325.9443

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16017-69-9.

Reference:
Article; Esvan, Yannick J.; Zeinyeh, Wael; Boibessot, Thibaut; Nauton, Lionel; Thery, Vincent; Knapp, Stefan; Chaikuad, Apirat; Loaec, Nadege; Meijer, Laurent; Anizon, Fabrice; Giraud, Francis; Moreau, Pascale; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 170 – 177;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 16017-69-9

Stage 1: ethyl 4-amino-2-chloro-5-iodobenzoate An iodine solution in ethanol was admixed with silver(I) sulphate and ethyl 4-amino-2-chlorobenzoate and then stirred at room temperature for 45 min. The reaction mixture was filtered through a frit and the filtrate was concentrated under reduced pressure. The residue was slurried in EtOAc, and dilute sodium hydrogencarbonate solution was added. Once everything had gone into solution, the aqueous phase was removed and sodium thiosulphate was dissolved therein. The organic phase was washed again with the aqueous phase and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate) gave 1.85 g (74% of theory) of ethyl 4-amino-2-chloro-5-iodobenzoate. HPLC-MS: logP=2.95; mass (m/z): 326.0 (M+H)+; 1H NMR (CD3CN) 1.32 (t, 3H), 4.27 (q, 2H), 5.01 (br. s, 2H), 6.80 (s, 1H), 8.16 (s, 1H).

The synthetic route of 16017-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Intellectual Property GmbH; Heil, Markus; Heilmann, Eike Kevin; Holmwood, Graham; Jeschke, Peter; Maue, Michael; Kapferer, Tobias; Reidrich, Matthias; Becker, Angela; Malsam, Olga; Losel, Peter; Voerste, Arnd; Goergens, Ulrich; Andree, Roland; US2014/88167; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics