Structure of 79477-87-5
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| CAS No. : | 79477-87-5 |
| Formula : | C8H5FO3 |
| M.W : | 168.12 |
| SMILES Code : | O=C(O)C(C1=CC=CC(F)=C1)=O |
| MDL No. : | MFCD07698679 |
| InChI Key : | ZBVBBDBIFKYALY-UHFFFAOYSA-N |
| Pubchem ID : | 13548098 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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.

[ 99556-60-2 ]
[ 79477-87-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydroxide; In ethanol; | (c) 3.8 g (0.02 mole) of 3-fluorophenylglyoxylic acid in 10 ml of ethanol are slowly added dropwise to a solution of 5.4 g (0.022 mole) of 1-amino-2-methyl-3-methylaminoguanidine hydroiodide in 55 ml of 2N hydrochloride acid. The temperature rises from 20 to 30 C. during this addition and a pale yellow precipitate forms. This mixture is stirred for 2 hours to a temperature in the range from 60 to 70 C., whereupon a clear yellow orange solution forms. After cooling, this solution is neutralised with an aqueous solution of sodium hydroxide. The precipitate is then isolated, washed with water and dried at 70 C., affording 4.3 g (76% of theory) of 3,4-bis(methylamino)-6-(3-fluorophenyl)-4H-1,2,4-triazin-5-one with a melting point of 173-174 C. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid;pH 7.4;Kinetics; | A series of compounds were synthesized and kinetically analyzed (Table 1). The measured rate constants correlate well with the Hammett ς parameters giving a p value of 3.80 (Figure 4). Many of the compounds display faster reactivity with Η202 than BFA. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 60% | With pyridine; selenium(IV) dioxide; at 90 - 110℃; for 5h; | General procedure: The substituted phenylglyoxylic acid were prepared from oxidation of corresponding acetophenone with SeO2: acetophenone (5 mmol), SeO2 (6 mmol), 20 mL of pyridine were added in a 50 mL round-bottom flask. The reaction was carried out at 110 C for 1 hour, then temperature was lowered to 90 C and the reaction was continued stirring at this temperature for 4 hours. The desired products were isolated by silica-gel columnchromatography in excellent yield (40%-79%). |
| With selenium(IV) dioxide; In pyridine; at 110℃; for 18h;Sealed tube; | General procedure: A flame-dried pressure tube was charged with the specified acetophenone (4.0 mmol,1.0 equiv.) and selenium dioxide (0.89 g, 8.0 mmol, 2.0 equiv.). Dry pyridine (5 mL)was added, the tube was sealed, and the reaction mixture was heated at 110 C for 18h. Afterwards, the reaction was cooled to room temperature and filtered. The filtratewas acidified with 1 M HCl solution and extracted three times with EtOAc.Subsequently, the combined organic layers were extracted three times with 1 M NaOHsolution. The combined aqueous layers were acidified with conc. HCl and extractedthree times with EtOAc. The combined organic layers were dried over Na2SO4 andconcentrated in vacuo. Purification by column chromatography yielded the products2b-2l. The characteriza-tion results are consistent with the references. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With hydrogenchloride; sodium dichromate; In water; at 95℃; for 6h; | General procedure: The specific synthesis method is: Add 1-(2-chlorobenzene) ethyl-1-one (0.15g, 1.0mmol) and 50mL trifluorotoluene to the flask,Stir to dissolve 1-(2-chlorobenzene) ethyl-1-one in trifluorotoluene, then add 2N HCl (0.5mL),Sodium dichromate (0.30g, 2.0mmol) was then added under acidic conditions, heated to 95C and reacted at this temperature under reflux for 6h.After the reaction, the trifluorotoluene in the system was removed, and sodium hydroxide was added to the aqueous phase to adjust the aqueous phase to pH 9 to remove impurities,Then add hydrochloric acid to the water phase to adjust the pH of the water phase to 3 and extract,Petroleum ether was recrystallized to obtain the product 2-(2-chlorobenzene)-2-glyoxylic acid (0.17g) in a 90% yield. |
| With pyridine; selenium(IV) oxide; at 100℃; for 4h; | General procedure: A pyridine solution (27 mL) containing 1-(3-methoxyphenyl)ethanone (8.00 g) and selenium dioxide (8.87 g) was stirred at an outside temperature of 100 C. for 4 hours. After cooling, the reaction solution was filtered through Celite (registered trademark). The filtrate was diluted with EtOAc, followed by washing with an aqueous 1 mol/L HCl solution and brine and drying with Na2SO4. The solvent was distilled off under reduced pressure to yield the title compound (10.6 g, gray solid). MS (ESI neg.) m/z: 179 ([M-H]-). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 453 mg | With hydrogenchloride; In ethanol; isopropyl alcohol; at 20℃; for 16h; | A solution of 2 mol/L HCl in IPA (0.669 mL) was added to a suspension of the compound (150 mg) prepared in Reference Example P-A6 and the compound (197 mg) prepared in Reference Example P-L4 in EtOH (3.0 mL), followed by stirring at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure to yield the title compound (453 mg, brown solid) MS (ESI pos.) m/z: 372 ([M+H]+). |
[ 25563-14-8 ]
[ 79477-87-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | With ammonium peroxydisulfate; palladium diacetate; In tetrahydrofuran; at 20℃; for 3h;Sealed tube; Green chemistry; | General procedure: A solution of benzamides (0.5 mmol), α-oxocarboxylic acids (0.6 mmol), Pd(OAc)2 (10 mol%) and(NH4)2S2O8 (4 mmol) in THF (3 mL) was stirred in a sealed tube under air at room temperature for 3 h.The reaction mixture was diluted with EtOAc and filtered through a pad of Celite. The filtrate waswashed with saturated aqueous Na2CO3 to remove the acid. The organic layer was dried over anhydrousNa2SO4 and filtered, and the solvent was removed under vacuum or in vacuo to provide the crude product.The purification was performed by flash column chromatography on silica gel (eluent: petroleumether/EtOAc = 4/1, v/v) to give 3-hydroxyisoindolin-1-ones. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 53% | With chloro-trimethyl-silane; magnesium; In N,N-dimethyl-formamide; at 20℃; | General procedure: A typical procedure is as follows. Magnesium turnings (0.36 g, 15 mmol) for Grignard reagent with no pre-treatment were placed in a 100 mL four-necked flask and were heated to dry. Carbon dioxide was introduced to the flask and a balloon filled with carbon dioxide was attached to the flask. Chlorotrimethylsilane (3.17 mL, 25 mmol) in dry DMF (30 mL) was added to the flask and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl benzoate 1a (0.72 mL, 5 mmol) was added dropwise by means of a syringe and the reaction mixture was stirred at room temperature until the starting material disappeared. Then the reaction mixture was carefully poured into 1 M hydrochloric acid solution (100 mL) and the product was extracted with diethyl ether (40 mL) four times. The combined organic layer was washed with 1 M potassium carbonate solution (40 mL) twice and the product was transferred to the water layer. To the combined water layers, 3 M hydrochloric acid (200 mL) was added and the product was extracted with ether (40 mL) four times. The combined ether layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the product 2a. |


[ 79477-87-5 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 4 g | With di-tert-butyl peroxide; copper(ll) bromide; In acetonitrile; at 60℃; under 760.051 Torr; for 24h; | 1 g (0.5 mmol, 50 mg), 2 g (0.6 mmol, 101 mg), acetonitrile (3 mL), copper bromide (0.05 mmol, 11 mg) and di-tert-butyl peroxide (1 mmol, 183 μL) were sequentially added to the reaction tube. The reaction was stirred at 60 C for 24 h under an air (1 atm) atmosphere. The reaction was then quenched with EtOAc (EtOAc) (EtOAc) Filtration, spin-drying, and silica gel column separation (petrole ether / ethyl acetate = 5 / 1) gave 4 g of the desired product |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With di-tert-butyl peroxide; copper(ll) bromide; In acetonitrile; at 60℃; under 760.051 Torr; for 24h; | 1d (0.5mmol, 102mg) was added to the reaction tube in turn.2e (0.6mmol, 101mg),Acetonitrile (3mL),Copper bromide (0.05 mmol, 11 mg) and di-tert-butyl peroxide (1 mmol, 183 μL),The reaction was stirred at 60 C for 24 h under an air (1 atm) atmosphere.Then the reaction was quenched by adding 10 mL of saturated brine.Extract with ethyl acetate (10 mL × 3), and combine the organic phases.It was dried over anhydrous sodium sulfate.Filter, spin dry,The silica gel column was separated (petroleum ether / ethyl acetate = 5 / 1) to give the desired product 3 g. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 35% | With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide; In dichloromethane; water; at 40℃; | General procedure: N-heteroarene (1 mmoL, 80 mg), α-keto acid (3 mmol), Formic acid (1 mmol, 38 μL), ammonium persulfate (3 mmoL, 685 mg), ferrous sulfate heptahydrate (0.08 mmoL, 22 mg) and 20 mL of mixed solvent (DCM: H2O = 3: 1) , 0.1 mL DMSO was added into a 25 mL round-bottomed flask. The mixture was stirred at 40 oC until TLC analysis indicating that the reaction was complete (witnessed by the disappearance of the N-heteroarene). After separation of organic phase, the residue was neutralized by 0.1 M sodium hydroxide solution, then extracted with DCM (3×20 mL), combined the organic phases, dried over Na2SO4, and concentrated in vacuo. The residue was N-heteroarene (1 mmoL, 80 mg), α-keto acid (3 mmol), Formic acid (1 mmol, 38 μL), ammonium persulfate (3 mmoL, 685 mg), ferrous sulfate heptahydrate (0.08 mmoL, 22 mg) and 20 mL of mixed solvent (DCM: H2O = 3: 1) , 0.1 mL DMSO was added into a 25 mL round-bottomed flask. The mixture was stirred at 40 oC until TLC analysis indicating that the reaction was complete (witnessed by the disappearance of the N-heteroarene). After separation of organic phase, the residue was neutralized by 0.1 M sodium hydroxide solution, then extracted with DCM (3×20 mL), combined the organic phases, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of petroleum ether/EtOAc (v : v = 20 : 1) as eluent to afford the desired pure product. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | With ammonium peroxydisulfate; palladium diacetate; In diethylene glycol dimethyl ether; at 78℃; for 12h;Green chemistry; | 0.2 mmol of 2-(1H-indol-1-yl)aniline, 0.01 mmol of palladium acetate, 0.4 mmol of ammonium persulfate and 0.4 mmol of 3-fluorobenzoic acid were sequentially added to the reaction tube. Then, 2 ml of diethylene glycol dimethyl ether was added as a solvent, and the reaction was stirred at 78 C for 12 hours, the reaction was stopped, cooled to room temperature and filtered, and the filtrate was extracted with ethyl acetate three times, and the organic phase was combined and used. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness, and then evaporated, and then purified by column chromatography. The column chromatography was used as a mixture of petroleum ether and ethyl acetate in a volume ratio of 55:1. Pure 6-(3-fluorophenyl)indolo[1,2-a]quinoxaline was obtained in a yield of up to 82%. |
[ 783-08-4 ]
[ 79477-87-5 ]
[ 79477-87-5 ]


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