190516-85-9|7-Methoxyquinolin-4(1H)-one| Ambeed

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CAS No. :	190516-85-9
Formula :	C₁₀H₉NO₂
M.W :	175.18
SMILES Code :	O=C1C=CNC2=C1C=CC(OC)=C2
MDL No. :	MFCD00169015

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

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%).

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Prevention
Code	Phrase
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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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.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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CAS No.: 190516-85-9

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CAS No.: 190516-85-9

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

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed