[ CAS No. 190516-85-9 ] {[proInfo.proName]}

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Quality Control of [ 190516-85-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 190516-85-9 ]

SDS Specification

Alternatived Products of [ 190516-85-9 ]

Product Details of [ 190516-85-9 ]

CAS No. :	190516-85-9	MDL No. :	MFCD00169015
Formula :	C₁₀H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	175.18	Pubchem ID :	-
Synonyms :

Safety of [ 190516-85-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 190516-85-9 ]

* 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.

Upstream synthesis route of [ 190516-85-9 ]
Downstream synthetic route of [ 190516-85-9 ]

[ 190516-85-9 ] Synthesis Path-Upstream 1~3

1
[ 190516-85-9 ]
[ 68500-37-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 100℃; for 1 h;	3-Methoxyaniline (1.23 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.90 g) were dissolved in 2-propanol (40 ml), and the mixture was stirred at 70°C for one hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with ether to give 5-[(3-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dio xan-4,6-dione (1.22 g, yield 44percent). 5-[(3-Methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.22 g) and biphenyl (5.1 g) were suspended in diphenyl ether (15 ml), and the mixture was stirred at 220°C for 1.5 hr. The reaction mixture as such was purified by column chromatography with a methanol-chloroform system to give 7-methoxy-1H-quinolin-4-one (394 mg, yield 51percent). 7-Methoxy-1H-quinolin-4-one (394 mg) was suspended in diisopropylethylamine (3 ml), phosphorus oxychloride (1 ml) was added to the suspension, and the mixture was stirred at 100°C for one hr. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 4-chloro-7-methoxyquinoline (312 mg, yield 72percent).

Reference： [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 46
[2] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 907 - 923

2
[ 190516-85-9 ]
[ 181950-57-2 ]

Reference： [1] European Journal of Medicinal Chemistry, 2019, p. 666 - 678

3
[ 190516-85-9 ]
[ 178984-56-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2019, p. 666 - 678

[ 190516-85-9 ] Synthesis Path-Downstream 1~6

1
[ 190516-85-9 ]
[ 68500-37-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With trichlorophosphate; for 3h;Heating;	A mixture of 7-methoxyquinolin-4(1H)-one 6 (10mmol) and phosphorous oxychloride (30mL) was heated for 3h. Most of phosphorous oxychloride was removed by evaporation under reduced pressure, and the residue was poured into ice water. Then, the mixture was made alkaline with ammonium hydroxide; the precipitate formed was collected by filtration, washed well with water and dried in a vacuum; and compound 7 was obtained as white solid (1.7g, 88%). ESI-MS m/z 194 [M+H]+. 1H NMR (300MHz, CDCl3): delta 8.67 (1H, d, J= 4.8Hz, ArH), 8.09 (1H, d, J= 9.0Hz, ArH), 7.42 (1H, d, J= 2.4Hz, ArH), 7.33 (1H, d, J= 4.8Hz, ArH), 7.28 (1H, dd, J=9.0Hz, J=2.4Hz, ArH), 3.97 (3H, s, CH3). 13C NMR (75MHz, CDCl3) delta 161.3, 151.0, 150.2, 142.4, 125.3, 121.7, 120.8, 119.3, 107.7, 55.9.
88%	With trichlorophosphate; for 2h;Reflux;	General procedure: A mixture of 7-substituted 4(1H)-quinolones 6a-d (10 mmol)and phosphorus oxychloride (30 mL) was heated for 2 h. Most ofphosphorus oxychloride was removed by evaporating underreduced pressure and the residue was poured into ice-water. Thenthe mixture was made alkaline with ammonium hydroxide and theprecipitate formed was collected by filtration, washed well withwater and dried in vacuum.
72%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 100℃; for 1h;	3-Methoxyaniline (1.23 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.90 g) were dissolved in 2-propanol (40 ml), and the mixture was stirred at 70C for one hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with ether to give 5-[(3-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dio xan-4,6-dione (1.22 g, yield 44%). 5-[(3-Methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.22 g) and biphenyl (5.1 g) were suspended in diphenyl ether (15 ml), and the mixture was stirred at 220C for 1.5 hr. The reaction mixture as such was purified by column chromatography with a methanol-chloroform system to give 7-methoxy-1H-quinolin-4-one (394 mg, yield 51%). 7-Methoxy-1H-quinolin-4-one (394 mg) was suspended in diisopropylethylamine (3 ml), phosphorus oxychloride (1 ml) was added to the suspension, and the mixture was stirred at 100C for one hr. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 4-chloro-7-methoxyquinoline (312 mg, yield 72%).

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 162,p. 666 - 678
[2]European Journal of Medicinal Chemistry,2019,vol. 178,p. 154 - 167
[3]Patent: EP1724268,2006,A1 .Location in patent: Page/Page column 46
[4]European Journal of Medicinal Chemistry,2013,vol. 63,p. 907 - 923

2
[ 89691-67-8 ]
[ 77287-34-4 ]
[ 42465-53-2 ]
[ 3219-34-9 ]
[ 190516-85-9 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2609 - 2612

3
[ 879-56-1 ]
[ 190516-85-9 ]

Reference： [1]Australian Journal of Chemistry,2011,vol. 64,p. 454 - 470

4
[ 71083-05-1 ]
[ 190516-85-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 63,p. 907 - 923
[2]European Journal of Medicinal Chemistry,2019,vol. 162,p. 666 - 678
[3]European Journal of Medicinal Chemistry,2019,vol. 178,p. 154 - 167

5
[ 190516-85-9 ]
[ 178984-56-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 162,p. 666 - 678

6
[ 190516-85-9 ]
[ 181950-57-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 162,p. 666 - 678
[2]European Journal of Medicinal Chemistry,2019,vol. 178,p. 154 - 167

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P304	IF INHALED:
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P311	Call a POISON CENTER or doctor/physician.
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P314	Get medical advice/attention if you feel unwell.
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P320
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P321
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P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P353	Rinse skin with water/shower.
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P378
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P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 190516-85-9 ] {[proInfo.proName]}

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Application In Synthesis of [ 190516-85-9 ]

[ 190516-85-9 ] Synthesis Path-Upstream 1~3

[ 190516-85-9 ] Synthesis Path-Downstream 1~6

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