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

InChI

InChI=1S/C11H13ClN2O3/c1-3-17-11(15)10(12)14-13-8-4-6-9(16-2)7-5-8/h4-7,13H,3H2,1-2H3

InChIKey

ATNPZEGMKLGIFA-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(Cl)=NNC1=CC=C(OC)C=C1

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(27143-07-3)Related Product Information

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