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Quinocetone

Quinocetone structure

CAS No:
81810-66-4
Formula:
C18H14N2O3
Chemical Name:
Quinocetone
Synonyms:
2-Propen-1-one,1-(3-methyl-1,4-dioxido-2-quinoxalinyl)-3-phenyl-;2-Propen-1-one,1-(3-methyl-2-quinoxalinyl)-3-phenyl-,N,N′-dioxide;1-(3-Methyl-1,4-dioxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one;NSC 621477;Quinocetone;871487-59-1;850339-82-1
Categories:
Active Pharmaceutical Ingredients > Veterinary Raw Materials

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Quinocetone Basic Attributes

Molecular Weight：

306.32

Exact Mass：

306.32

EC Number：

1312995-182-4

Characteristics

PSA：

63.4

XLogP3：

2.4

Density：

1.22

Melting Point：

187-188 °C

Flash Point：

302.7±32.9 °C

Refractive Index：

1.625

Quinocetone Use and Manufacturing

Methods of Manufacturing

in 250 mLIn a three-necked flask, After adding 64 mL of methanol and 5.05 g (0.0455 mol) of anhydrous CaCl2, the mixture was dissolved with stirring and then added dropwise3.70 g (0.0344 mol)HydroxyEthylamineFormateSub-liquid, Further, 20.25 g (0.1908 mol) of benzaldehyde was added, the temperature was raised to 50 ° C with stirring, 37.50 g (0.1718 mol)Acetylmethylquine, Slowly heated to 60-65 ° C, The reaction was incubated for 3 hours, TThe LC traces the reaction to the end point and stops the reaction. Cooling down to 25 ° C, suction filtration, Washed 3 times with methanol, Drained, Vacuum drying, To give 49.98 g of a bright yellow powdery solid, M.p. 189-191 ° C, Product purity 98.7percent, Yield 95.0percent.A mixture of 2-acetyl-3-methyl-quinoxaline 1, 4-dioxide (2) (8.09 g, 0.040 mol) andbenzaldehyde (6.37 g, 0.060 mol) in 50 mL ethanol was heated at 70 °C for 30 min to obtain aclear solution, and then 4-(dimethylamino)pyridinium acetate (0.364 g, 2.0 mmol), readilyprepared according to literature, 9 was added to the solution. The solution was then stirred at70 °C for 3 h. On cooling the solution to 0 °C, yellow crystals precipitated within 3 h. Theyellow crystals were collected by filtration, washed with ethanol, and air-dried. The motherliquor was evaporated to recycle the catalyst 4-(dimethylamino)pyridinium acetate. Recrystallizationof the yellow crystals afforded compound 3. Yield: 12.3 g (95 percent). Analytical andspectral data for 3 are presented in the Supplementary material to this paper.Anhydrous magnesium sulfate (1.2 g, 0.01 mol) was added to 100 mL of methanol to stir and dissolve, and 1.05 g (0.01 mol) of diethanolamine was added.Anhydrous acetic acid 0.3g (0.005mol), stirring to dissolve after adding benzaldehyde 6.4g (0.06mol), dissolved directly after adding dissolved 2-acetyl-3-methylquinoxaline-1, 4-dioxide 10g (0.046mol), heated to 55 ° C, the reaction began, the system first clarified and precipitated Solid, keep warm for 4 hours, The reaction is complete. Cool to room temperature and hold at room temperature for more than 2 hours. Crystallize and filter to obtain crude quinocetone, Wash the cake thoroughly with fresh methanol, Dry to obtain the product 13.1g, yield 94percent, 98.5percent purity.In 500 ml reactor was added 100 ml of ethanol, benzofurazan 13.6 g (0.1 mol), acetyl acetone 20 g (0.2 mol), benzaldehyde 22 g (0.2 mol), magnetic Mg-Al hydrotalcite solid base catalyst 6 grams, tributylbenzyl basic quaternary ammonium salt 11 grams, at 50 ° C for 1 hour, the reaction is completed, filter out the solid base catalyst, the filtrate with activated carbon treatment, Place precipitated pale yellow solid product was filtered and dried to give the cake quinocetone 24.5 g, 80percent yield.

Uses

Used as antibacterial, anti-diarrhea, and growth-promoting new livestock and poultry feed additives

Computed Properties

Molecular Weight:306.3
XLogP3:2.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:306.10044231
Monoisotopic Mass:306.10044231
Topological Polar Surface Area:63.4
Heavy Atom Count:23
Complexity:547
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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