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Chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Apixaban intermediate
Product Name: | Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate |
Synonyms: | 2-chloro-2-[2-(4-methoxyphenyl)hydrazinylidene];ethyl 2-chloro-2-[(4-methoxyphenyl)hydrazinylidene]acetate;Apixaban Impurity B;(Z)-Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate (Apixaban);Apixaban-2;1-(4-methoxyphenyl)-4-(2-((4-(2-oxopiperidin-1-yl)phenyl)amino)ethyl)-1H-pyrazole-3,5-dicarboxamide;Chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester;Ethyl chloro[(4-methoxyphenyl)hydrazono]acetate |
CAS: | 27143-07-3 |
MF: | C11H13ClN2O3 |
MW: | 256.69 |
EINECS: | 608-053-7 |
Product Categories: | 27143-07-3 |
Mol File: | 27143-07-3.mol |
Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Chemical Properties |
Melting point | 94℃ |
Boiling point | 349.0±44.0 °C(Predicted) |
density | 1.23 |
storage temp. | 2-8°C |
solubility | Chloroform (Sparingly), Methanol (Slightly) |
form | Solid |
pka | 11.63±0.10(Predicted) |
color | Yellow to Dark Yellow |
Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Usage And Synthesis |
Physical properties | Light yellow to dark yellow solid |
Uses | Acetic acid, 2-chloro-2-[2-(4-methoxyphenyl)hydrazinylidene], ethyl ester is an ester derivative and can be used as an intermediate in the synthesis of apixaban. |
Synthesis | Step-1:Water (600 ml) was added to p-anisidine (100 g) at room temperature and the resulting mixture was cooled to 10°C, followed by the addition of concentrated hydrochloric acid (133.5 g). The resulting mixture was cooled to —5°C to 0°C, followed by portion-wise addition of 40 % aqueous sodium nitrite solution over 45 minutes to 1 hour. The resulting mass was stirred for 1 hour 30 minutes at —5°C to0°C, followed by slow addition of 11 % sulfamic acid solution over 1 hour to 1 hour 30 minutes to produce a reaction mass (first part).Step-2:Sodium acetate (146 g) was added to water (300 ml) at room temperature and then stirred for 10 minutes to 15 minutes, followed by the addition of ethyl 2-chloroacetoacetate (160.4g) and acetone (300 ml) at room temperature to form a reaction mixture. The resulting mixture was cooled to 0°C. The resulting mixture was added to the reaction mass (first part) obtained in step-i at —5°C to 0°C and then stirred for 1 hour at the same temperature. Acetone (200 ml) was added to the resulting mass and stirred for 30 minutes at —5°C to 0°C. The resulting mass was settled for 5 hours at —5°C to 0°Cand then filtered the solid. Methanol (150 ml) was added to the resulting solid at room temperature and then stirred for 2 hours at the same temperature. Ethyl 2-chloro-2-(2-(4-methoxyphenyl) hydrazone)acetate was obtained through further purity. |
Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Preparation Products And Raw materials |
Raw materials | p-Anisidine-->Ethyl 4-chloroacetoacetate |
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