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CAS No. : | 67805-67-8 | MDL No. : | MFCD08741409 |
Formula : | C9H6BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HGJBIJWBYATVQY-UHFFFAOYSA-N |
M.W : | 224.05 | Pubchem ID : | 10933094 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | at 140℃; for 3 h; | Step 2C: Preparation of 2,8-dibromoquinolme:; A mixture of 8-bromoquinolin-2(lH)-one (5 g, 22 mmol) and phosphoryl tribromide (13 g, 45 mmol) was heated to 140°C for three hours. The resulting mixture was poured onto 100 g of ice and 100 ml water. The mixture was stirred for 1 hour and the resulting solids were filtered to yield the title compound. (5.1 g, 80 percent yield) MS APCI (+) 286, 288, and 290 (M+l of each isotope combination) detected. |
80% | Stage #1: at 140℃; for 3 h; Stage #2: at 0℃; for 1 h; |
A mixture of 8-bromoquinolin-2(lH)-one (5 g, 22 mmol) and phosphoryl tribromide (13 g, 45 mmol) was heated to 140°C for three hours. The resulting mixture was poured onto 100 g of ice and 100 ml water. The mixture was stirred for 1 hour and the resulting solids were filtered to yield the title compound. (5.1 g, 80 percent yield) MS APCI (+) 286, 288, and 290 (M+l of each isotope combination) detected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; trichlorophosphate; | c. 8-bromo-2-chloro-quinoline A suspension of 2.8 g (12.49 mmol) of 8-bromo-1H-quinoline-2-one in 20 ml of phosphorus oxychloride is refluxed for 90 minutes and the reaction mixture is cooled and then added dropwise to 200 ml of water. The aqueous solution is made basic with concentrated ammonia solution, the precipitate formed is filtered off and washed with water. Yield: 2.8 g (92.4% of theory), Melting point: 115 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With phosphorus(V) oxybromide; at 140℃; for 3h; | Step 2C: Preparation of 2,8-dibromoquinolme:; A mixture of 8-bromoquinolin-2(lH)-one (5 g, 22 mmol) and phosphoryl tribromide (13 g, 45 mmol) was heated to 140C for three hours. The resulting mixture was poured onto 100 g of ice and 100 ml water. The mixture was stirred for 1 hour and the resulting solids were filtered to yield the title compound. (5.1 g, 80 % yield) MS APCI (+) 286, 288, and 290 (M+l of each isotope combination) detected. |
80% | A mixture of 8-bromoquinolin-2(lH)-one (5 g, 22 mmol) and phosphoryl tribromide (13 g, 45 mmol) was heated to 140C for three hours. The resulting mixture was poured onto 100 g of ice and 100 ml water. The mixture was stirred for 1 hour and the resulting solids were filtered to yield the title compound. (5.1 g, 80 % yield) MS APCI (+) 286, 288, and 290 (M+l of each isotope combination) detected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
b. 8-bromo-1H-quinoline-2-one 6 g (22.21 mmol) of N-(2-bromo-phenyl)-3-ethoxy-acrylamide are added batchwise to 30 ml of concentrated sulphuric acid (exothermic) and stirred for one hour. The reaction mixture is poured onto ice water and the precipitate formed is filtered off. The product is purified by column chromatography on silica gel (eluant: dichloromethane/ethyl acetate=3:1). Yield: 2.95 g (59.3% of theory), Melting point: 186 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; dimethyl sulfate; In methanol; water; | EXAMPLE 2 (Procedure B) One gram of sodium hydroxide was dissolved in 15 ml. of methanol, and 4.5 g. of 8-bromocarbostyril was added to the solution at room temperature. Thereafter, 2.6 g. of dimethyl sulfate was added dropwise thereto. The reaction mixture was boiled for 3 hours, cooled to room temperature and poured into 50 ml. of water. The precipitated crystals were filtered, dried and recrystallized from ethanol to obtain 3.9 g. of 8-bromo-1-methylcarbostyril (m.p. 106-107 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; | (c) 8-Bromo-2-(methyloxy)quinoline To a suspension of 8-bromo-2(1H)-quinolinone (2.76 g, 12.32 mmol) in N,N-dimethylformamide (40 ml) under an argon atmosphere at 0C was added potassium carbonate (3.4 g, 24.63 mmol). The reaction was then stirred for 15 minutes before methyl iodide (0.91 ml, 14.78 mmol) was added. The reaction was allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture was then evaporated and the residue treated with dichloromethane and water. The aqueous fraction was re-extracted with dichloromethane. The combined organic fractions were then dried (MgSO4), the solvent was removed under reduced pressure and then the residue was subjected to chromatography on silica gel using a methanol-dichloromethane gradient. This provided the desired compound as a yellow solid (2.16 g, 74%). MS (ES+) m/z 239 (MH+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Step 2B: Preparation- of 8-bromoquinolin-2(TH>one:; A mixture of N-(2- bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 1000C for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65 % yield) MS ESI (+) m/z 224 and 226 (M+l of each isotope) detected. | |
65% | A mixture of N-(2- bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 1000C for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65 % yield) MS ESI (+) m/z 224 and 226 (M+l of each isotope) detected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | (c) 8-Bromo-2-(methyloxy)quinoline To a suspension of 8-bromo-2(1H)-quinolinone (2.76 g, 12.32 mmol) in N,N-dimethylformamide (40 ml) under an argon atmosphere at 0 C. was added potassium carbonate (3.4 g, 24.63 mmol). The reaction was then stirred for 15 minutes before methyl iodide (0.91 ml, 14.78 mmol) was added. The reaction was allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture was then evaporated and the residue treated with dichloromethane and water. The aqueous fraction was re-extracted with dichloromethane. The combined organic fractions were then dried (MgSO4), the solvent was removed under reduced pressure and then the residue was subjected to chromatography on silica gel using a methanol-dichloromethane gradient. This provided the desired compound as a yellow solid (2.16 g, 74%). MS (ES+) m/z 239 (MH+, 100%). | |
74% | To a suspension of 8-bromo-2(lH)-quinolinone (2.76 g, 12.32 mmol) in N5N- dimethylformamide (40 ml) under an argon atmosphere at O0C was added potassium carbonate (3.4 g, 24.63 mmol). The reaction was then stirred for 15 minutes before methyl iodide (0.91 ml, 14.78 mmol) was added. The reaction was allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture was then evaporated and the residue treated with dichloromethane and water. The aqueous fraction was re- extracted with dichloromethane. The combined organic fractions were then dried (MgSO4), the solvent was removed under reduced pressure and then the residue was subjected to chromatography on silica gel using a methanol-dichloromethane gradient. This provided the desired compound as a yellow solid (2.16 g, 74%). MS (ES+) m/z 239 (MH+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 120℃; for 1h;Inert atmosphere; | Step 4.1 : 8-Naphthalen-1-yl-1 H-quinolin-2-oneA mixture of 8-bromo-2(1H)-quinolinone [1.98 g, 8.84 mMol (synthesis see: Eur. J. Org. Chem. 2003, 1559)] and 1-naphthaleneboronic acid (1.84 g, 10.7 mMol) in 19 ml K2CO3 (1 M in H2O) and 9 ml DMF is degassed by 3 times evacuation and flushing with N2. Then Pd(PPh3)2CI2 (380 mg, 0.53 mMol) is added and the mixture is heated to 120 0C for 60 min. After filtration, the filtrate is diluted with water and EtOAc, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and partially concentrated. The resulting suspension is filtered, the title compound washed with ice cold EtOAc and dried in HV at 40 0C: m.p.: 198-199 0C; MS: [M+1]+ = 272. More product can be isolated from the filtrate by chromatography (Combi Flash; CH2CI2/acetone 99:1 → 92:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 5.1 : 8-Bromo-6-nitro-1 H-quinolin-2-oneTo an ice cooled solution of 8-bromo-1 H-quinolin-2-one [190.0 g, 0.848 MoI (synthesis see: Eur. J. Org. Chem. 2003, 1559)] in 836 ml TFA, 304 ml of fuming HNO3 is added via an addition funnel over 90 min and the temperature is kept between 0 and 5 0C. The dark reaction mixture is stirred for 7 h at rt and then poured into 2 kg of ice/water. Vigorously stirring, warming up to rt, filtration, washing with water, sat. NaHCO3 and again water with subsequent drying gives the title compound: m.p.: decomp. > 250 0C; MS: [M+1]+ = 249 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 2h;Sealed tube; Inert atmosphere; | In a sealed tube under Argon, to a solution of <strong>[67805-67-8]8-bromoquinolin-2(1H)-one</strong> (200 mg, 0.89 mmol, 1.0 eq.) and Bis(pinacolato)diboron (453 mg, 1.79 mmol, 2.0 eq.) in 1 ,4-dioxane (4 mL) was added KOAc (175 mg, 1.79 mmol, 2.0 eq.). The reaction mixture was sparged with argon for 10 min before addition of Pd(dppf)CI2 (33 mg, 0.05 Eq, 44.6 pmol). The reaction mixture was heated at 110C for 2 h. The reaction mixture was filtered through a pad of Celite and the cake was washed with EtOAc (30 mL). Filtrate was hydrolyzed NH4Clsat. (40 mL), then extracted twice with EtOAc (40 mL). Combined organic layers were washed with brine (50 mL), dried over magnesium sulfate and concentrated. The crude was purified by flash chromatography (Si02, DCM/MeOH: 100/0 to 95/5) to afford compound 89 (200 mg, 82%) as an orange solid. M/Z (M+H)+: 272.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.2 g | To a suspension of 5.63 g (140 mmol, 60% wt. in mineral oil) of NaH in 1000 mL of dry tetrahydrofuran (THF) was added 30.0 g (134 mmol) of 8-bromoquinolin-2(lH)-one in small portions at 0C. After that the reaction mixture was stirred for 30 min at room temperature. The solution obtained was cooled to 0C, and 20.2 g (134 mmol) of i |
Tags: 67805-67-8 synthesis path| 67805-67-8 SDS| 67805-67-8 COA| 67805-67-8 purity| 67805-67-8 application| 67805-67-8 NMR| 67805-67-8 COA| 67805-67-8 structure
[ 67805-53-2 ]
8-Bromo-1-methylquinolin-2(1H)-one
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[ 67805-53-2 ]
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[ 67805-53-2 ]
8-Bromo-1-methylquinolin-2(1H)-one
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[ 67805-53-2 ]
8-Bromo-1-methylquinolin-2(1H)-one
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[ 67805-53-2 ]
8-Bromo-1-methylquinolin-2(1H)-one
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