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CAS No. : | 16090-33-8 | MDL No. : | MFCD00269642 |
Formula : | C6H5NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VIIYYMZOGKODQG-UHFFFAOYSA-N |
M.W : | 155.11 | Pubchem ID : | 4313918 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
60% | With potassium carbonate In acetone at 20℃; for 10 h; | To a 100-mL round-bottom flask was placed a solution of 2-nitrobenzene-1,4-diol (1 g,6.45 mmol) in acetone (15 mL) then K2C03 (4.45 g,32.20 mmol) and (bromomethyl)benzene (2.64 g,15.48mmol) were added. Thereaction was stirred for 10 h at rt,filtered,and concentrated under reduced pressure affording1.302 g (60percent) of the title compound as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium peroxydisulfate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; nitric acid man verseift das Reaktionsprodukt mit verd. Kalilauge; | ||
Multi-step reaction with 2 steps 1: glacial acetic acid; concentrated nitric acid | ||
Multi-step reaction with 2 steps 1: alcohol; nitric acid / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With hydrogen bromide; acetic acid at 110℃; for 28h; | |
With hydrogen bromide; acetic acid | ||
With hydrogen bromide for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate at 100℃; im geschlossenen Rohr; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With borane-ammonia complex; copper(II) oxide In methanol at 50℃; for 0.333333h; | |
With methanol; nickel | ||
With hydrogenchloride; tin |
In tetrahydrofuran | 1.d (d) (d) 2-aminohydroquinone The 2-nitrohydroquinone (24.6 g, 0.159 mole) in THF (250 ml) was reduced under 60 Atm. hydrogen at 60° C. in the presence of Ni Raney catalyst in an autoclave. The resulting amine was not isolated due to easy oxidation by air oxygen. | |
With hydrogen In ethanol for 2h; | 21.A Example 21 ; [Show Image] N-(4-(benzo[d]oxazol-6-yloxy)-3-methylphenyl)6-(2-methoxyethoxy)quinazolin-4-amine Step A: Preparation of 2-aminobenzene-1,4-diol: To a solution of 2-nitrobenzene-1,4-diol (3.00 g, 19.34 mmol) in ethanol (100 mL) was added 10% palladium on carbon (0.600 g, 0.564 mmol). After shaking under 40 psi of hydrogen for 2 hours, the mixture was filtered and the filtrated was concentrated under reduced pressure to provide the product as solid. | |
With 10% Pd/C; hydrogen In methanol at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; air |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; ammonium persulfate; water Ansaeuern mit verd. Schwefelsaeure; | ||
With sodium hydroxide; ammonium peroxydisulfate | ||
With dihydrogen peroxide In acetonitrile Irradiation; |
With potassium hydroxide; K5<Cu(H2TeO6)2> In water at 35℃; | ||
With potassium hydroxide; K5<Cu(H2TeO6)2> In water at 20℃; various concentrations of the substrates; | ||
With glucose-6-phosphate; D-glucose-6-phosphate dehydrogenase; NADP; magnesium chloride; ascorbic acid In methanol at 37℃; aq. phosphate buffer; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium hydroxide for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 7% 2: 2% 3: 4% 4: 25% | With silver(l) oxide In benzene for 8h; 1) 0 deg C, 2) roomtemp.); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tert.-butylnitrite; silica gel In acetonitrile at 100℃; Microwave irradiation; | |
95% | With Vilsmeier reagent; potassium nitrate In neat (no solvent) at 100℃; Microwave irradiation; | |
90% | With tert.-butylnitrite In acetonitrile at 29.84℃; |
82% | With potassium hydrogensulfate; sodium perborate hexahydrate; sodium nitrite In neat (no solvent) for 0.0180556h; Molecular sieve; Microwave irradiation; regioselective reaction; | Microwave (MW)-assisted procedure for synthesis of nitrocompounds General procedure: Reactants such as sodium nitrite (12 mmol), with aromatic or heteroaromatic compound (10 mmol), KHSO4 (1 mmol), and SPB (1 mmol), were thoroughly mixed with silica gel and placed in MW oven. Reaction progress was monitored by thin-layer chromatography (TLC) until completion. The reaction mixture was then treated with NaHCO3 solution and extracted with ethyl acetate (30 mL). Final product was obtained by using the same workup steps as detailed in the preceding section. Sodium perborate/NaNO2/KHSO4-initiated nitration reactions with several other compounds also afforded corresponding nitroderivatives (Scheme 1) via both conventional and MW-assisted reactions. |
81% | With nitric acid; vanadia; silica gel at 150℃; for 0.025h; Microwave irradiation; regioselective reaction; | Typical Experimental Procedure for Microwave-AssistedNitration (MWANR) of Organic Compounds General procedure: The microwave (MW) reactor used was of CEM make, which was equipped with temperature, pressure, and MW power control units. An oven-dried MW vial was charged with a mixture containing aromatic compound, V2O5 (9 mg, 0.005 mmol) and 69% HNO3 (0.063 mL, 1 mmol) and silica gel slurry, and irradiated in a MW (power input 140 W) at 150 °C for few minutes. After completion of the reaction, as as certained by TLC, the reaction mixture was treated with sodium bicarbonate; the organic layer was diluted with dichloromethane (DCM) and separated from aqueous layer. The crude product mixture was purified with ethyl acetate DCM mixture. The purity was checked with TLC. The products were identified by characteristic spectroscopic data. |
80% | With bismuth(III) nitrate; sulfuric acid; silica gel at 25℃; for 0.166667h; | |
68% | With uronium nitrate In water; acetonitrile at 80℃; for 0.666667h; Microwave irradiation; regioselective reaction; | General procedure: Phenol (10 mmol) and urea nitrate (10 mmol)were mixed together in acetonitrile-water (95:5, 5 ml) in a 25 ml round bottomed flask and placed in a Milestone’s Start SYNTH microwave reactor. The reaction mixture was heated at 80°C for 40-50 min. At the end of the reaction, the reaction mixture was allowed to cool at room temperature,treated with water, and extracted with dichloromethane. After removing the solvent under reduced pressure, the residue was purified by column chromatography on silica gel to give the corresponding nitrophenol. In allcases ortho-nitrophenols were obtained selectively without any evidence forthe formation of the para-substituted nitrophenols. All the compoundsobtained were characterized by 1H NMR, 13C NMR, mp (for solids), GC-MSand in comparison with authentic samples. |
60% | With fuming sulphuric acid; nitric acid at 25 - 90℃; for 4h; | |
33.5% | With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In diethyl ether for 2h; Ambient temperature; | |
Multi-step reaction with 3 steps 1: sodium bicarbonate 2: glacial acetic acid; concentrated nitric acid | ||
20.3 %Chromat. | With tetrasodium 5,10,15,20-tetra(4-sulfophenyl)porphyrinatoiron(II); dihydrogen peroxide; sodium nitrite In aq. phosphate buffer at 25℃; for 1.33333h; Green chemistry; regioselective reaction; | 2.2 General Procedure of Nitration of Phenols General procedure: To a solution contained phosphate sodium buffer (50 mL, 0.1 M, pH 7.0), phenols (1 mmol) and NaNO2 (50-60 mmol), H2O2 (30 % aqueous solution, 3 mmol) was added dropwise in 80 min. The reaction was initiated by adding metalloporphyrin (50-60 mg) at room temperature. After stirring for 80 min, the reaction products were extracted several times with chloroform or ethyl acetate, and the organic phase was combined, dried with sodium sulfate. The organic solvent was removed under vacuum.The residue was dissolved in methanol and quantitatively analyzed by HPLC. |
With Prussian blue; potassium hydrogensulfate; sodium nitrite In water; acetonitrile at 20℃; Darkness; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With manganese(IV) oxide; magnesium sulfate In benzene Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With silver(II) oxide; magnesium sulfate In dichloromethane for 1.33333h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With manganese(IV) oxide; nitric acid; magnesium sulfate In dichloromethane at 0℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) H2SO4, (ii) /BRN= 607898/, Py; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium peroxynitrite In phosphate buffer at 20 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Oxidation mit Hg(ClO4)2; | ||
Rk. mit 2,9-CH3-phenanthrolin, k, ΔG(excit.), ΔGgrad; | ||
Hydroxylierung; |
Rk. mit Hg(ClO4)2: k, τ; | ||
Ox.unter voltammetr.Beding.in Acetonitril -> 2-Nitro-benzochinon-(1,4); | ||
Anod.Hydroxylier.unter voltammetr.Beding.in 2M Perchlorsaeure -> 2-Nitro-1,3,4-Trihydroxy-benzol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
m-Nitrophenol, bact. Metabolismus; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide at 100℃; im geschlossenen Rohr; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 46% 2: 27% | With sodium sulfate; silver(l) oxide In dichloromethane at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature 3: 92 percent / formic acid / 0 °C 4: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 5: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 6: 62 percent / TBAF / tetrahydrofuran / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature 3: 92 percent / formic acid / 0 °C 4: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature 3: 92 percent / formic acid / 0 °C 4: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 5: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature 3: 92 percent / formic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: MnO2/HNO3, MgSO4 / CH2Cl2 / 30 h / 0 °C 2: CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: MnO2/HNO3, MgSO4 / CH2Cl2 / 30 h / 0 °C 2: CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: MnO2/HNO3, MgSO4 / CH2Cl2 / 30 h / 0 °C 2: CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: MnO2/HNO3, MgSO4 / CH2Cl2 / 30 h / 0 °C 2: CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In water; at 10 - 35℃; for 5.0h; | A suspension of 2-nitrobenzene-1,4-diol (1.00 g) and 10% palladium carbon (containing water (50%), 1.00 g) in 1 M hydrochloric acid (13 mL) was stirred at room temperature for 5 hr under a hydrogen atmosphere. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the obtained solid was washed with ethyl acetate to give the title compound (949 mg).1H NMR (300 MHz, DMSO-d6) delta 6.60 (1H, dd, J=8.7, 2.6 Hz), 6.73 (1H, d, J=2.6 Hz), 6.80 (1H, d, J=8.7 Hz), 9.20 (1H, brs), 9.54 (2H, brs), 9.78 (1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water in alk. soln.; | ||
In water in alk. soln.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | ||
82% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 5 h / 10 - 35 °C 2.1: pyridine / 3 h / Reflux 3.1: N,N-dimethyl-formamide; thionyl chloride / 0.08 h / 60 °C 3.2: 1.5 h / 10 - 35 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 60 °C / Inert atmosphere 5.1: hydrogenchloride / ethyl acetate / 0.25 h / 10 - 35 °C 5.2: 0.17 h / 10 - 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 5 h / 10 - 35 °C 2: pyridine / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 5 h / 10 - 35 °C 2.1: pyridine / 3 h / Reflux 3.1: N,N-dimethyl-formamide; thionyl chloride / 0.08 h / 60 °C 3.2: 1.5 h / 10 - 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 5 h / 10 - 35 °C 2.1: pyridine / 3 h / Reflux 3.1: N,N-dimethyl-formamide; thionyl chloride / 0.08 h / 60 °C 3.2: 1.5 h / 10 - 35 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 5 h / 10 - 35 °C 2.1: pyridine / 3 h / Reflux 3.1: N,N-dimethyl-formamide; thionyl chloride / 0.08 h / 60 °C 3.2: 1.5 h / 10 - 35 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere 5.1: hydrogenchloride / ethyl acetate / 0.25 h / 10 - 35 °C 5.2: 0.17 h / 10 - 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 5 h / 10 - 35 °C 2.1: pyridine / 3 h / Reflux 3.1: N,N-dimethyl-formamide; thionyl chloride / 0.08 h / 60 °C 3.2: 1.5 h / 10 - 35 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 10% Pd/C; hydrogen / methanol / 2 h / 20 °C 2: pyridine / tetrahydrofuran / 0.08 h / 20 °C 3: Oxone; tetrabutylammomium bromide / water; acetonitrile / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 10% Pd/C; hydrogen / methanol / 2 h / 20 °C 2: pyridine / tetrahydrofuran / 0.08 h / 20 °C 3: Oxone; tetrabutylammomium bromide / water; acetonitrile / 0.5 h / 20 °C 4: magnesium bis(monoperoxyphthalate)hexahydrate / tetrahydrofuran; water / 0.33 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 10% Pd/C; hydrogen / methanol / 2 h / 20 °C 2.1: pyridine / tetrahydrofuran / 0.08 h / 20 °C 3.1: Oxone; tetrabutylammomium bromide / water; acetonitrile / 0.5 h / 20 °C 4.1: magnesium bis(monoperoxyphthalate)hexahydrate / tetrahydrofuran; water / 0.33 h / 20 °C 4.2: 11 h / 20 °C / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: 2-nitrohydroquinone With potassium carbonate In N,N-dimethyl-formamide; acetone at 60℃; for 0.5h; Stage #2: propargyl bromide at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium carbonate; In acetone; at 20℃; for 10.0h; | To a 100-mL round-bottom flask was placed a solution of 2-nitrobenzene-1,4-diol (1 g,6.45 mmol) in acetone (15 mL) then K2C03 (4.45 g,32.20 mmol) and (bromomethyl)benzene (2.64 g,15.48mmol) were added. Thereaction was stirred for 10 h at rt,filtered,and concentrated under reduced pressure affording1.302 g (60%) of the title compound as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 10 h / 20 °C 2: methanol; nickel(II) acetate tetrahydrate; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | Nucleophilic addition of 3-H indoles to nitroquinone (5a). General procedure: To a 4 mL glass vial, 3 (15.6 mg, 0.1 mmol) and Ag2O (46.4 mg, 0.2 mmol) were mixed as a suspension in DCE (0.5 mL) at r.t. Indole (14 mg, 0.12 mmol) was added fast as a solid, and then the reaction mixture was vigorously stirred overnight covered by aluminum foil. After the reaction was finished (monitored by TLC), the mixture was filtered through a short silica pad, and flushed by ethyl acetate 3 times. The solution was concentrated under vacuum and dry loaded on a silica column. The crude product was purified by flash column chromatography (ethyl acetate: hexane 1:2) gave 5a as a dark purple solid (23 mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). 1 H NMR (400 MHz, Acetone-d6) d = 10.12 (s, 1H), 7.61 (d, J = 8.0, 1H), 7.47 (d, J = 8.2, 1H), 7.25 (ddd, J = 8.2, 6.9, 1.1, 1H), 7.16-7.06 (m, 3H), 2.26 (s, 3H); 13C NMR (101 MHz, Acetone-d6) d = 185.99, 178.19, 139.32, 138.28, 135.90, 130.21, 129.40, 125.49, 122.02, 120.71, 120.60, 118.84, 112.73, 10.30; HRMS (ESIQTOF) calcd for C15H10N2O4 [M+H]+ 283.0713, found 283.0707. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; for 3h; Darkness; | General experimental procedure, nucleophilic addition of 3-alkylindoles to nitroquinone: (4a). General procedure: To a 5 mL round bottom flask charged with solid 3 (47 mg, 0.3 mmol, 1.0 equiv), Ag2O (139 mg, 0.6 mmol, 2.0 equiv) and CeCl3 anhydrous (74 mg, 0.3 mmol, 1.0 equiv), dichloroethane 3 mL was added followed by fast addition of 3-methylindole (43 mg, 0.33 mmol, 1.1 equiv). The reaction mixture was stirred at r.t. covered by aluminum foil for 3 h, and filtered through a silica pad. Solvent was removed under vacuum and the crude was loaded on column. Purification by flash column chromatography (ethyl acetate: hexane 1:2) gave the pure product as a brown solid (42 mg, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61 g | at 20℃; | 1.1 (1)Synthesis of 2-nitro-1,4-acetic acid phenyl diester 50 g of 2-nitrohydroquinone was added to 250 ml of acetyl chloride,Stir at room temperature overnight, concentrate under reduced pressure to remove the remaining acetyl chloride.Adding saturated aqueous sodium hydrogencarbonate solution and ethyl acetate for extraction.Separation, drying and concentration gave 61 g of 2-nitro-1,4-phenylacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.7 g | With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice; | 10 (Example 10) Production of compound represented by formula (II-10) Under a nitrogen atmosphere, 10.0 g of the compound represented by the formula (I-10-1), 3.2 g of pyridinium p-toluenesulfonate, and 100 mL of dichloromethane were added to a reaction vessel. While cooling with ice13.6 g of 3,4-dihydro-2H-pyran was added dropwise,Stir at room temperature for 8 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane.The organic layer was washed successively with water and brine.By performing purification by column chromatography (Wakogel 50NH2 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., dichloromethane/hexane),17.7 g of the compound represented by the formula (I-10-2) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / 20 °C / Inert atmosphere; Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 20 h / 0 - 3750.38 Torr |
Tags: 16090-33-8 synthesis path| 16090-33-8 SDS| 16090-33-8 COA| 16090-33-8 purity| 16090-33-8 application| 16090-33-8 NMR| 16090-33-8 COA| 16090-33-8 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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