Fenofibrate impurity A | Chlorides

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Quality Control of Fenofibrate impurity A Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Details of Fenofibrate impurity A

CAS No. :	42019-78-3
Formula :	C₁₃H₉ClO₂
M.W :	232.66
SMILES Code :	C2=C(C(C1=CC=C(Cl)C=C1)=O)C=CC(=C2)O
MDL No. :	MFCD00002357
InChI Key :	RUETVLNXAGWCDS-UHFFFAOYSA-N
Pubchem ID :	123504

Safety of Fenofibrate impurity A

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Fenofibrate impurity A

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 42019-78-3 ]

[ 42019-78-3 ] Synthesis Path-Downstream 1~35

1
[ 1871-38-1 ]
[ 42019-78-3 ]

References: [1]Journal of Physical Chemistry,1995,vol. 99,p. 12962 - 12970.
[2]Journal Of Scientific and Industrial Research,1956,vol. 15 B,p. 633.

2
[ 1871-38-1 ]
[ 42019-78-3 ]
[ 2985-79-7 ]

References: [1]Journal Of Scientific and Industrial Research,1956,vol. 15 B,p. 633.

3
[ 42019-78-3 ]
[ 52890-73-0 ]

References: [1]Journal Of Scientific and Industrial Research,1956,vol. 15 B,p. 633.
[2]Patent: EP1221441,2002,A2 .Location in patent: Page 55.
[3]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2522 - 2536.
[4]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2522 - 2536.

4
[ 4913-77-3 ]
[ 42019-78-3 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1920,vol. 39,p. 345.
Recueil des Travaux Chimiques des Pays-Bas,1922,vol. 41,p. 717.
[2]Recueil des Travaux Chimiques des Pays-Bas,1920,vol. 39,p. 345.
Recueil des Travaux Chimiques des Pays-Bas,1922,vol. 41,p. 717.

5
[ 71783-49-8 ]
[ 42019-78-3 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1920,vol. 39,p. 345.
Recueil des Travaux Chimiques des Pays-Bas,1922,vol. 41,p. 717.

6
[ 74-11-3 ]
[ 108-95-2 ]
[ 42019-78-3 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1955,vol. 75,p. 378,380.
Chem.Abstr.,1956,p. 2510.

7
[ 42019-78-3 ]
[ 59595-15-2 ]
[ 51318-41-3 ]

References: [1]Patent: DE2322853,1973, .
Chem.Abstr.,1974,vol. 80.

8
[ 122-01-0 ]
[ 100-66-3 ]
[ 42019-78-3 ]

References: [1]Farmaco, Edizione Scientifica,1986,vol. 41,p. 381 - 387.
[2]Patent: FR2300552,1976, .
Patent: DE2605382,1976, .
Chem.Abstr.,1976,vol. 85.

9
[ 67-66-3 ]
[ 42019-78-3 ]
[ 67-64-1 ]
[ 42017-89-0 ]

Yield	Reaction Conditions	Operation in experiment
73%		A mixture of 4-chloro-4'-hydroxybezophenone (116 g, 0.500 mole) and sodium hydroxide (120 g, 3.00 mole) in acetone (1 L) was heated to reflux for 2 hours. The heating was stopped and the heating source was removed. A mixture of chloroform (179 g, 1.50 mole) in acetone (300 mL) was added drop-wise. The reaction mixture was stirred overnight without heating. The mixture was heated to reflux for 8 hours and then allowed to cool to room temperature. The precipitate was removed by filtration and washed with acetone (100 mL). The filtrate was concentrated under reduced pressure to give a brown oil. Water (200 mL) was added to the brown oil and was acidified (to pH=l) with IN hydrochloric acid. The precipitate, which formed was filtered and dried under high vacuum. The remaining yellow solid (268 g) was recrystallized from toluene in 4 batches (400 mL toluene each). After filtration and drying under high vacuum, the experiment produced fenofibric acid (116 g, 73% yield) as a light yellow solid. 'H NMR (300 MHz, DMSO-d6): 6 = 13.22 (1H, s, br), 7.72 (4H, d, J= 8.4 Hz), 7.61 (2H, d, J= 7. 8 Hz), 6.93 (2H, d, J= 7. 8 Hz), 1.60 (6H, s). "C NMR (75 MHz, DMSO-d6) : 5 = 192.96, 174.18, 159.35, 136.84, 136.12, 131.67, 131.02, 129.12, 128. 43, 116. 91,78. 87,25. 13.
	With sodium hydroxide;	The Fenofibric acid is obtained by condensation, acidification and purification of 4-hydroxy-4-chlorobenzophenone with acetone and chloroform under the conditions of sodium hydroxide as a catalyst. Fenofibric acid (63.75 g, 0.2 mol) was added to a 500 ml flask. Isopropyl alcohol 69ml and water with toluene 100ml, After stirring and heating, after the reaction liquid reaches the specified temperature, the initial acid value of the reaction liquid is sampled and measured. At the same time, 10 g of the catalyst was added to the four-necked flask, and the timing was started, and the acid value was measured at regular intervals. In a boiling state, the water formed by the reaction is azeotropically distilled off with toluene.The aqueous phase was separated in a water separator and toluene was refluxed.As the reaction progresses, the temperature of the reaction solution gradually increases, and the temperature of the reaction solution is controlled to be within 110 C. After the reaction for a certain period of time, the reaction is stopped. The reaction solution was cooled, filtered, and neutralized with a mass concentration of 3% to 4% sodium hydroxide solution to pH = 7 to 8, and allowed to stand for stratification. The upper layer is dried with an appropriate amount of anhydrous sodium sulfate until clarification, and the clear liquid is taken. The toluene with water is distilled off under normal pressure and then under reduced pressure, and the distilled toluene is recycled. The material was cooled to 50 C, dissolved in isopropanol, cooled, filtered, and dried to obtain a yellowish crystalline powder, which was purified with isopropyl alcohol.A white solid of 66.69 g was obtained, and the esterification yield was 92.4% (based on fenofibrate acid), and the content was 99.9%.

References: [1]Patent: WO2005/46575,2005,A2 .Location in patent: Page/Page column 176-177.
[2]Patent: FR2300552,1976, .
Patent: DE2605382,1976, .
Chem.Abstr.,1976,vol. 85.
[3]Patent: CN109651144,2019,A .Location in patent: Paragraph 0023; 0026-0028; 0031-0033; 0036-0037.

10
[ 42019-78-3 ]
[ 535-11-5 ]
2-[4-(4-Chloro-benzoyl)-phenoxy]-propionic acid ethyl ester [ No CAS ]

References: [1]Patent: FR2300552,1976, .
Patent: DE2605382,1976, .
Chem.Abstr.,1976,vol. 85.

11
[ 123-75-1 ]
[ 50-00-0 ]
[ 42019-78-3 ]
[ 94042-64-5 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 295 - 298.

12
[ 42019-78-3 ]
[ 22197-31-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium hydroxide; In methanol; at 20℃;Inert atmosphere;	Example 8; 0.95m/m methanolic KOH 1.0036N was mixed into a solution of 1 mole of CHBP in 500ml of methanol under an N2 atmosphere. Then 0.07eq. of K2CO3 solid and 2.4gm of Zeolite MS 4A (as buffering agent) were added and the reaction mixture stirred at room temperature for 30 min. Then the methanol was distilled off under N2 to isolate K-CHBP. Into a 11 Hastelloy CRTM reactor, under an N2 flow of 5 l/hr, there was charged 0.35 moles K-CHBP and 1000 gms/mole of DPSO2. Heating over in 3 hrs reached 250°C and then that temperature was maintained for 2 hrs. After reaching 250°C the pressure was reduced to 100 mm Hg and maintained for 1 hr. The vacuum was then released with nitrogen and the reaction mass heated to 305°C in 1 hr. After reaching the desired viscosity the reaction mass was endcapped by reaction with methyl chloride. The polymer details are as set out in Table 5, below:

References: [1]Journal of the Chemical Society. Perkin transactions II,1988,p. 1729 - 1734.
[2]Patent: EP2105430,2009,A1 .Location in patent: Page/Page column 9.

13
[ 42019-78-3 ]
(4-Chloro-phenyl)-(4-hydroxy-phenyl)-methanone oxime [ No CAS ]

References: [1]Farmaco, Edizione Scientifica,1987,vol. 42,p. 117 - 124.

14
[ 2069-48-9 ]
[ 42019-78-3 ]

References: [1]Organometallics,2016,vol. 35,p. 3378 - 3387.
[2]Journal of the Chemical Society. Perkin transactions II,1988,p. 1729 - 1734.

15
[ 42019-78-3 ]
[ 621-29-4 ]
m-Tolyl-carbamic acid 4-(4-chloro-benzoyl)-phenyl ester [ No CAS ]