ChemicalBook CAS DataBase List N-(4-CYANO-PHENYL)-GLYCINE

N-(4-CYANO-PHENYL)-GLYCINE synthesis

7synthesis methods

Product Name:N-(4-CYANO-PHENYL)-GLYCINE
CAS Number:42288-26-6
Molecular formula:C9H8N2O2
Molecular Weight:176.17

79-08-3

873-74-5

42288-26-6

3.2.3 Preparation of [(4-cyanophenyl)amino]acetic acid (V). Molecular formula: C9H8N2O2. molecular weight: 176.17. Raw materials: 90g (0.75mol) of bromoacetic acid (F), 211.7g (1.5mol) of p-aminobenzonitrile (G), 35g (0.42mol) of sodium bicarbonate. Procedure: bromoacetic acid (F) and p-aminobenzonitrile (G) were mixed in 1250 ml of water to form a suspension. The suspension was placed in a bath heated to 100-110°C for 3 hours. Upon completion of the reaction, the reaction vessel was removed from the bath and cooled to room temperature, followed by further cooling in a refrigerator. The precipitate was separated by diafiltration and dried in a vacuum desiccator at 100 °C. Yield of crude product: 122 g (92.8% yield), HPLC purity: 97%. Purification step: the crude product was converted to sodium salt and re-acidified using aqueous sodium bicarbonate to release the free acid by dilute hydrochloric acid (1:1). After filtration, the product was washed with water and dried in a vacuum desiccator at 105°C. The product was then purified to a sodium salt using aqueous sodium bicarbonate. Yield of purified product: 115 g (88% yield), HPLC purity: 99.1%, water content: 0.13%, sulfated ash: 1.8%.

79-08-3 Synthesis

79-08-3
318 suppliers
$9.00/1g

873-74-5
660 suppliers
$9.00/1g

42288-26-6
560 suppliers
$14.00/1g

Yield:42288-26-6 88%

Reaction Conditions:

in water at 100 - 110; for 3 h;

Steps:

3
3.2.3 Preparation of [(4-cyanophenyl)amino]acetic acid (V) C₇H₆N₂ C2H3DPθ2 C₉H₈N₂O₂ MoI. Wt.: 1 18,14 MoI. Wt.: 138,95 MoI. Wt.: 176,17VIngredientsF: 90 g - 0.75 molG: 211.7 g - 1.5 molSodium bicarbonate: 35 g, 0.42 molThe starting substances F and G were mixed in 1250 ml of water and this suspension was inserted into a bath heated up to 100-110 ⁰C. After three hours of heating the reaction container was removed from the bath, cooled in the fridge and the separated substance was sucked off. The substance was dried in a vacuum drier at the temperature of 100 °C. Yield: Crude product: 122 g (92.8%), HPLC: 97%The crude product was purified by conversion to the sodium salt and re-acidification using an aqueous solution of sodium bicarbonate. The acid was released by means of diluted hydrochloric acid (1 :1). After sucking off and washing with water the product was dried in a vacuum drier (105 °C). Yield: Purified product: 115 g (88%), HPLC: 99.1%, water content: 0.13%; sulphate ash: 1.8%

References:

ZENTIVA, K.S. WO2009/111997, 2009, A1 Location in patent:Page/Page column 11

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