ChemicalBook CAS DataBase List (4-Carboxy-3-ethoxy)phenyl Acetic Acid (Repaglinide Impurity)

(4-Carboxy-3-ethoxy)phenyl Acetic Acid (Repaglinide Impurity) synthesis

5synthesis methods

Product Name:(4-Carboxy-3-ethoxy)phenyl Acetic Acid (Repaglinide Impurity)
CAS Number:220438-80-2
Molecular formula:C11H12O5
Molecular Weight:224.21

Benzoic acid, 4-(cyanomethyl)-2-ethoxy-, ethyl ester

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(4-Carboxy-3-ethoxy)phenyl Acetic Acid (Repaglinide Impurity)

220438-80-2
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$125.00/5mg

Yield: 96%

Reaction Conditions:

Stage #1:ethyl 4-cyanomethyl-2-ethoxy-benzoate with sodium hydroxide;water for 1.5 - 2 h;Heating / reflux;
Stage #2: with hydrogenchloride in water; pH=2 at 25 - 35; for 0.75 - 1 h;

Steps:

4 Example 4; Preparation of (4-Carboxy-3-ethoxy-phenyl) acetic acid (VI)
Charged 50 g (1.0 mol) of Ethyl-4-cyanomethyl-2-ethoxy benzoate to a solution of 250 ml of water and 26 g (3.0 mol) of sodium hydroxide. The resulted reaction mixture was heated to reflux for 1½ hr to 2 hr. Cooled the reaction mass to 25-35° C. and adjust the pH to around 2 with hydrochloric acid at 25-35° C., stirred for 45-60 minutes. Filtered the compound and washed with 100 ml of water. Dried the product at 70-80° C. The yield of the title compound is 46.1 g (96%). [0042] The obtained product was characterised by analytical techniques like IR, Mass and 1H-NMR

References:

DR. REDDY'S LABORATORIES LIMITED;DR. REDDY'S LABORATORIES, INC US2004/249188, 2004, A1 Location in patent:Page 2; 4; 5