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CAS No. : | 4101-30-8 | MDL No. : | MFCD00016646 |
Formula : | C10H13NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KGKWXEGYKGTMAK-UHFFFAOYSA-N |
M.W : | 195.22 | Pubchem ID : | 602085 |
Synonyms : |
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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: |
* 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 |
---|---|---|
55% | Stage #1: With sodium methylate In 1,2-dimethoxyethane at 20℃; for 16.5 h; Stage #2: With sodium ethanolate In 1,2-dimethoxyethane at 20℃; for 24 h; |
To a solution of 2-amino-4,5-dimethoxylacetophenone (4.5 g, 23 mmol) in DME (100 ml_) was added NaOMe (5.0 g, 92 mmol). The reaction was stirred for 30 min after which ethyl formate (8.5 g, 115 mmol) was added and the reaction mixture was stirred for 16 h at rt. Then NaOEt (21percent dispersion in oil, 22 g, 69.1 mmol) was <n="48"/>added and the reaction mixture was stirred for an additional 24 h at it Water (1OmL) was then added, and the mixture was stirred for 1 h, then concentrated under reduced pressure. The pH of the resulting aqueous mixture was adjusted to pH 7 using HCI (2N aqueous solution). The resulting precipitated was collected by filtration, and then successively washed with water, ethyl acetate and ethyl ether. The solid was dried under mechanical vacuum give 2.6 g (yield 55 percent) of the title compound.1H NMR (400 MHz, DMSO-cfe) δ 10.97 (bs, 1 H), 7.79 (d, 1 H), 7.42 (s, 1 H), 6.96 (s, 1 H), 5.96 (d, 1 H), 3.84 (s, 3 H), 3.81 (s, 3 H); ES-MS m/z 206.2 [M+H]+, LCMS RT (min) 1.21. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.7% | With iron(0); ammonia hydrochloride; In water monomer; ethyl acetate; at 20℃; for 4h; | Compound II 3.40g placed in a 250ml four-necked flask,A mixed solution of ethyl acetate and water (34 ml / 20 ml) was added.At room temperature,To the stirred reaction flask was added 3.55 g of ammonium chloride (0.06644 mol, 4.4 eq).And reduced iron powder 5.92g (0.1057mol, 7eq),The reaction system was then heated to 20 C and stirred for 4 h.The progress of the reaction was checked by TLC.After the substrate is completely reacted, the excess iron powder is filtered out.The filter cake was rinsed three times with 15 ml of ethyl acetate.The organic layer was separated from the filtrate and washed with saturated brine.Concentration under reduced pressure gave Compound I 2.79 g, yield: 94.7%, HPLC purity: 99.2%. |
61.4% | With hydrogen; acetic acid;5%-palladium/activated carbon; In methanol; at 40℃; under 1471.14 Torr; for 8h; | Methanol (5.4 L), acetic acid (433 g), and 5% palladium/carbon (162 g) were added to 3,4-dimethoxy-6-nitroacetophenone (1082 g), and the mixture was stirred under a hydrogen gas pressure of 2 Kg/cm2 at 40C for 8 hr. The reaction solution was filtered and was then washed with methanol (1 L). The filtrate was neutralized with an aqueous sodium hydroxide solution and was then concentrated under the reduced pressure. Water (10 L) was added to the concentration, and the mixture was stirred overnight, was then filtered, and was washed with water (7 L). Toluene (4 L) was added to the filtered product, and the mixture was heated to 80C and was stirred for 1 hr. The reaction solution was decanted while hot, and the residue was then concentrated under the reduced pressure. The residue was filtered, was washed with toluene (300 mL) and was dried under the reduced pressure to give 2-amino-4,5-dimethoxyacetophenone (576 g, yield 61.4%). 1H-NMR (400 MHz, CDCl3/ppm); δ 2.56 (s, 3H), 3.84 (s, 3H), 3.88 (s, 3H), 6.10 (s, 1H), 7.11 (s, 1H) |
30% | With iron(0); acetic acid; In ethanol; water monomer; at 100℃; for 2h;Inert atmosphere; | <strong>[4101-32-0]1-(4,5-dimethoxy-2-nitrophenyl)ethan-1-one</strong> (8 g) and iron powder (20 g) were added to a mixture of HOAc (70 mL), water (100 mL) and EtOAc (20 mL). The reaction was carried out at 100 C for 2 hours, and the pH was adjusted to 7 with sodium bicarbonate aqueous solution. The reaction solution was added with 400 mL of ethyl acetate, filtered, concentrated. The resulting residue was recrystallized from ethyl acetate-petroleum ether to obtain 1-(4,5-dimethoxy-2-aminophenyl)ethan-1-one (1.37 g, 30%). |
palladium monocarbide; In methanol; | Example E 6-Amino-3,4-dimethoxyacetophenone A slurry of 1 equivalent of 3,4-dimethoxy-6-nitroacetophenone in methanol is treated with Pd/C (10%) and the mixture is hydrogenated at 45 psi for 24 hours. The residue after filtration and removal of solvent is crystallized from ethyl alcohol to afford purified product, mp=98-100 C.; δTMSCDCl3 2.50 (s, 3H, CH3), 3.80-3.85 (2s, 3H ea., OCH3); 6.05, 7.05 (2s, 1H ea., C2 H, C5 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium hydrogencarbonate In chloroform; triethylamine | 23 2'-(N-3-Carbethoxypropylamino)-4',5'-dimethoxyacetophenone EXAMPLE 23 2'-(N-3-Carbethoxypropylamino)-4',5'-dimethoxyacetophenone Ethyl-4-bromobutyrate (190.7 g, 978 mM) was added with stirring to 2'-amino-4',5'-dimethoxyacetophenone (31.8 g, 163 mM) in triethylamine (33.9 mM) and the reaction mixture was heated at 110° C. for one hour. After cooling to room temperature 100 mL of 2% NaHCO3 was added and the reaction mixture was stirred for sixteen hours. A yellow solid formed which was dissolved in CHCl3 (250 mL). The aqueous phase was extracted with CHCl3 (4*200 mL), the organic extracts were combined and dried over MgSO4, filtered, and the solvent removed in vacuo to give a semisolid residue. The residue was chromatographed on SilicAR CC-7 and the appropriate fractions were crystallized upon standing from ether to afford the title compound in 62% yield,,mp 74°-76° C. |
61% | With triethylamine at 110℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine In dichloromethane at 0 - 20℃; | |
With triethylamine In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | at 130 - 135℃; for 2h; | |
With acetic acid for 2h; Heating; | ||
With boron trifluoride diethyl etherate at 140℃; for 18h; | 2 SYNTHETIC PREPARATION 2; Synthesis of 4-Methyl-6,7-dimethoxyquinazoline; 2-Amino-4,5-dimethoxyacetophenone (5.0 g) and boron trifluoride etherate (1.5 mL) were heated in formamide (80 mL) at 140 0C for 18 h. The reaction mixture was cooled to room temperature and extracted three times with benzene. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. Flash chromatography on silical gel, eluting with a mixture of 98/2 dichloromethane/methanol gave 4-methyl-6,7-dimethoxyquinazoline (D-1) as a yellow solid, 3.43 g; 1H NMR (CDCI3, 300 MHz) 8.99 (s, 1 H), 7.30 (s, 1 H), 7.18 (s, 1 H), 4.05 (s, 6H), 2.87 (s, 1 H) ppm; MS (ES) 205 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; sodium nitrite In water at -5 - 75℃; for 5.16667h; | 6,7-Dimethoxycinnolin-4-ol (7) Commercially available l-(2-amino-4,5-dimethoxyphenyl)ethanone (5) (2.0 g, 10.0 mmol) was dissolved in 1 N hydrochloric acid (100 mL) and cooled to -5 °C, then a solution of sodium nitrite (0.7 g, 10.0 mmol) in water (4 mL) was added over a period of 10 min. The mixture was stirred at 0 °C for 1 h then heated to 60 - 75 °C for 4 h. After the reaction was complete it was again cooled to 0 °C and the resulting precipitate was collected via filtration to give 7 as a light tan solid (1.75 g, 85%). |
80.5% | With hydrogenchloride; sodium nitrite In water at -5 - 60℃; for 4h; | 1-(2-Amino-4,5-dimethoxyphenyl)ethanone 2 (10.0 g,51.3 mmol) was added to the mixture of concentrated HCl400 mL and water 50 mL. A solution of sodium nitrite (3.6g, 51.3 mmol) in water of 1000 mL was added to the reactionmixture under -5 oC. Then stirred at 60 °C for 4 h, the solutionwas cooled to room temperature and filtered. The solidwas washed by ethanol to obtain compound 3 8.5 g, 80.5%yield. 1 H NMR (400 MHz, DMSO-d6): 13.33 (s, 1H,OH), 7.65 (s, 1H, ArH), 7.30 (s, 1H, ArH), 6.96 (s, 1H,ArH), 3.85 (s, 6H, 2CH3), ESI-MS [M+H]+, m/z: 207.1. |
78% | With hydrogenchloride; sodium nitrite In water at -5 - 75℃; for 5.75h; | 1 l-(2-Amino-4,5-dimethoxyphenyi)ethanone (15.60 g, 0.07991 mol) was dissolved in concentrated hydrogen chloride in water (555 mL) and water (78 mL). The mixture was cooled to -5° C (ice/brine) and a solution of sodium nitrite (5.55 g, 0.0804 mol) in water (20 mL) was added over a period of 45min. The mixture was stirred another 1 h at 0° C and then warmed to 60-75° C for 4 h. The mixture was then cooled to room temperature using an ice bath and the resulting precipitate was collected via filtration. The solid HC1 salt was added to about 1.0 L of water and then basified to pH ~12 with NaOH. The resulting brown solution was neutralized with HC1 and the resulting precipitate was collected to provide 12.77 g (78%) of 6,7-dimethoxycinnolin-4-ol as a light tan solid, which was used without further purification. MS [M+H] = 207. *H NMR (DMSO 66) 8 (ppm) 7.62 (s, 1H), 7.30 (s, 1H), 6.93(s, 1H), 3.89 (s, 3H), 3.85 (s, 3H). |
78% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; sodium nitrite In water at -5 - 75℃; for 5.75h; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In water | B.1 [00177] Step 1. l-(2-Amino-455-dimethoxyphenyl)ethanone (15.60 g, 79.91 mmol) was dissolved in concentrated hydrogen chloride in water (555 mL) and water (78 tnL). The mixture was cooled to -5° C and a solution of sodium nitrite (5.55 g, 80.4 mmol) in water (20 mL) was added over a period of 45 minutes. The mixture was stirred for an additional 1 h at 0° C and then warmed to 60-75° C for 4 h. The mixture was then cooled to room temperature using an ice bath and the resulting precipitate was collected via filtration. The solid hydrochloride salt thus obtained was added to approximately 1.0 L of water and then basified to pH ~12 with sodium hydroxide. The brown solution was neutralized with hydrochloric acid, and the resulting precipitate was collected to provide 12.77 g of 6,7-dimethoxycinnolin- 4-ol as a light tan solid (78% yield), which was used without further purification. MS [M+H] = 207. 1H NMR (DMSO d6) δ (ppm) 7.62 (s, IH), 7.30 (s, IH), 6.93(s, IH), 3.89 (s, 3H)3 3.85 (s, 3H). |
71% | With hydrogenchloride; sodium nitrite In water at 75℃; | |
13.78 g | With hydrogenchloride; sodium nitrite In water for 6h; Cooling with ice; Heating; | |
With hydrogenchloride; sodium nitrite In water at 0 - 70℃; for 2.75h; | 6.1 6,7-Dimethoxycinnolin-4-ol Step 1: 6,7-Dimethoxycinnolin-4-ol 1-(2-Amino-4,5-dimethoxyphenyl)ethanone (105 g, 0.538 μmol) was dissolved in concentrated HCl (2000 mL, 20 μmol) at ambient temperature. The solution was then cooled to 0-4° C., and sodium nitrite (37.5 g, 0.543 μmol) was added dropwise over 45 minutes as a solution in water (200 mL). The reaction mixture was stirred at 0-4° C. for one hour during which time it turned dark brown and became homogenous. The reaction mixture was then heated to 60-70° C. for four hours, and a yellow solid formed. After cooling the reaction mixture to 10° C., the solid was collected by filtration. The wet solid was suspended in 1500 mL of water, and the pH was adjusted to 12 with 4N NaOH to give a brown solution, followed by adjusting the pH to 7 with concentrated hydrochloric acid (78 mL). 6,7-Dimethoxycinnolin-4-ol precipitated as an off-white solid, which was filtered, washed with water (3*300 mL), and dried in a vacuum overnight at 50° C. | |
Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; sodium nitrite In water at 0 - 70℃; for 5h; Stage #2: With sodium hydroxide; water In water | 6.1 Example 6Synthesis of 4-Bromo-6,7-dimethoxycinnoline; Step 1 : 6,7-Dimethoxycinnolin-4-ol l-(2-Amino-4,5-dimethoxyphenyl)ethanone (105 g, 0.538 mol) was dissolved in concentrated HCl (2000 mL, 20 mol) at ambient temperature. The solution was then cooled to 0-4 0C, and sodium nitrite (37.5 g, 0.543 mol) was added dropwise over 45 minutes as a solution in water (200 mL). The, reaction mixture was stirred at 0-4 0C for one hour during which time it turned dark brown and became homogenous. The reaction mixture was then heated to 60-700C for four hours, and a yellow solid formed. After cooling the reaction mixture to 10 0C, the solid was collected by filtration. The wet solid was suspended in 1500 mL of water, and the pH was adjusted to 12 with 4N NaOH to give a brown solution, followed by adjusting the pH to 7 with concentrated hydrochloric acid (78 mL). 6,7-Dimethoxycinnolin-4-ol precipitated as an off-white solid, which was filtered, washed with water (3 x 300 mL), and dried in a vacuum overnight at 50 0C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dmap In dichloromethane at 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: 2-amino-4,5-dimethoxyacetophenone; 2-chloro-4,5-dihydro-1H-imidazole In dichloromethane at 20℃; for 17h; Stage #2: With sodium hydroxide In water for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogenchloride; sodium methylate In tetrahydrofuran; water | 1.4 Method 4 Method 4 Tetrahydrofuran (6 ml) was added to 2-amino-4,5-dimethoxy-acetophenone (300 mg, 1.5 mmol) to form a solution. To this solution was added sodium methoxide (250 mg, 4.6 mmol), and the mixture was stirred at room temperature for 60 minutes. Ethyl formate (0.5 ml, 7.7 mmol) was then added, and the mixture was stirred at room temperature for an additional 150 minutes. After adding water (3 ml) to the reaction solution, and stirring for 30 minutes, 10% hydrochloric acid was added to the mixture for neutralization, thereby causing precipitation. The precipitate was collected by filtration, washed with water (3 ml*2), and then purified by silica gel column chromatography to give 310 mg of the desired product (yield 98%). 1H-NMR (DMSO-d6, 500 MHz): δ 3.82 (s, 3H), 3.86 (s, 3H), 5.94 (d, J=7.3 Hz, 1H), 6.96 (s, 1H), 7.44 (s, 1H), 7.76 (d, J=7.3 Hz, 1H), 11.52 (s, 1H). Mass Spectrometry (FD-MS, m/z): 205 (M+). |
95% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With sodium methylate In 1,2-dimethoxyethane at 20℃; for 1.16667h; Stage #2: formic acid ethyl ester In 1,2-dimethoxyethane at 20℃; for 2h; | |
95% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With sodium methylate In 1,2-dimethoxyethane at 20℃; for 1.16667h; Stage #2: formic acid ethyl ester In 1,2-dimethoxyethane for 2h; Further stages.; |
95% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With sodium methylate In 1,2-dimethoxyethane at 20℃; for 0.5h; Stage #2: formic acid ethyl ester In 1,2-dimethoxyethane at 20℃; for 1h; Stage #3: With hydrogenchloride; water In 1,2-dimethoxyethane for 0.166667h; | 1.A A) 6,7-Dimethoxyquinolin-4(1H)-one To a solution of 1-(2-amino-4,5-dimethoxyphenyl)ethanone (9.80 g, 50 mmol, Lancaster Synthesis LTD) in DME (300 mL) at rt was added NaOMe (15.0 g, 278 mmol), and the mixture was stirred for 30 minutes at rt. To this mixture was added ethyl formate(25 mL) dropwise with stirring at rt. After an hour the reaction was quenched by adding aq HCl (50 mL of 2N HCl), stirred for 10 minutes and the precipitate was filtered, washed with a small amount of H2O and EtOAc to obtain the 1st crop of product. To the filtrate solution was added EtOAc (200 mL), the EtOAc layer was separated, the aqueous layer was washed with EtOAc (200 mL), and the combined EtOAc solution was dried over MgSO4, concentrated in vacuo and the residue was triturated with a small amount of CH3OH/EtOAc to obtain the 2nd crop of product. The solids of 1st crop and 2nd crop were combined, mixed with water (100 mL), stirred for 10 minutes, the solid was filtered and dried to obtain the product (9.75 g, 95%) as a white solid. 1H NMR (DMSO-d6) δ8.50 (s, 1H), 7.75 (d, 1H, J=4.2 Hz), 7.42 (s, 1H), 7.08 (s, 1H), 5.91 (d, 1H, J=4.2 Hz), 3.83 (s, 3H), 3.80 (s, 3H). |
81.5% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With sodium methylate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: formic acid ethyl ester In tetrahydrofuran at 0 - 20℃; for 1h; | 3 (3) Step of cyclization: Tetrahydrofuran (THF) (5.3 L) and sodium methoxide (313 g) were added to 2-amino-4,5-dimethoxyacetophenone (337 g), and the mixture was stirred at 20°C for 30 min. Ethyl formate (858 g) was added to the reaction solution at 0°C, and the mixture was stirred at 20°C for one hr. Water (480 mL) was added thereto at 0°C, and the mixture was neutralized with 1 N hydrochloric acid. The resultant precipitate was collected by filtration, and the filtered product was slurried in water (2 L) for washing. The slurry was filtered, and the filtered product was then dried under the reduced pressure to give 6,7-dimethoxy-4-quinolone (352 g, yield 81.5%). 1H-NMR (400 MHz, DMSO-d6/ppm); δ 3.81 (s, 3H), 3.84 (s, 3H), 5.94 (d, 1H), 7.01 (s, 1H), 7.43 (s, 1H), 7.76 (d, 1H) |
68% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With sodium methylate In 1,2-dimethoxyethane at 20℃; for 0.5h; Stage #2: formic acid ethyl ester In 1,2-dimethoxyethane at 20℃; for 2h; Stage #3: With hydrogenchloride In 1,4-dioxane at 50℃; for 1h; | 11 To a solution of 2′-amino-4′,5′-dimethoxyacetophenone (4.9 g, 25 mmol) in dimethoxyethane (150 mL) was added sodium methoxide (7.5 g, 0.14 mol), and the reaction mixture was stirred at room temperature for 30 minutes. Ethyl formate (12 mL, 0.15 mol) was added thereto. After stirring the reaction mixture at room temperature for 2 hours, 2 mol/L hydrochloric acid (25 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and then concentrated in vacuo. To the residue was added 4 mol/L hydrogen chloride in dioxane (30 mL). After stirring the reaction mixture at 50° C. for one hour, the reaction mixture was cooled to room temperature, and the generated solid was collected on a filter and dried to give Compound (A-2) (3.5 g, 68% yield). LC/MS (Condition (1)): [M+H]+/Rt=206/0.42 min |
With sodium methylate | 16.A (A) 4 - [(6,7-dimethoxy-quinolin-4-yl) oxy] aniline 2-acetyl-4,5-dimethoxy-ethyl aniline and cyclization occurs too quinolinone, phosphine oxychloride chlorinated 4-chloro-6,7-dimethoxy-quinoline, and then under alkaline conditions with p-aminophenol reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With lithium diisopropyl amide In tetrahydrofuran; n-heptan1ol; ethylbenzene for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In N,N-dimethyl-formamide at 60 - 70℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With pyridine In dichloromethane at 20℃; | |
79% | With pyridine at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium tetrahydroborate In ethanol for 1h; Heating; | |
With sodium tetrahydroborate In ethanol; ethyl acetate Cooling; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium methylate 2: trichlorophosphate 3: potassium <i>tert</i>-butylate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: Et3N / CHCl3 / 0.05 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 68 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 56 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 82 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 56 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 48 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 73 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 73 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 80 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 84 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 93 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 21 percent / toluene / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 68 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C 1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C 2.1: POCl3 / Heating 3.1: Heating 4.1: H2; Et3N / Pd(OH)2/C / dimethylformamide / 20 °C 5.1: 55 percent / toluene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; potassium hydroxide; triethylamine In tetrahydrofuran; hexane; ethyl acetate | E.12.24 24 24 Compound 95 2-Acetyl-4,5-dimethoxyaniline (2.0 g) was dissolved in tetrahydrofuran (50 ml), and to the mixture were added triethylamine (2.2 g) and dimethylaminopyridine (400 mg), and then a solution of cyclopropylcarbonyl chloride (1.7 g) in tetrahydrofuran (5 ml). The mixture was stirred at room temperature for 3 hours. After the addition of a 10% aqueous solution of potassium hydroxide, the mixture was stirred and extraction was conducted with chloroform. The extract was washed with saturated saline and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 50 g). Elution with a mixed solvent of n-hexane (60 parts) and ethyl acetate (40 parts) gave N-cyclopropylcarbonyl-2-acetyl-4,5-dimethoxyaniline (2.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethylenesulfonyl fluoride; acetic acid | 14 2-[(2-Acetyl-4,5-dimethoxyphenyl)amino]ethenesulfonyl Fluoride EXAMPLE 14 2-[(2-Acetyl-4,5-dimethoxyphenyl)amino]ethenesulfonyl Fluoride To a mixture of 2-amino-4,5-dimethoxyacetophenone (18 g, 92 mmol) in 125 mL of glacial acetic acid was added in one portion ethenesulfonyl fluoride (11.4 g, 0.1 mol) under nitrogen. After stirring for 1 hour at room temperature the resulting yellow mixture was refluxed for 1 hour. The yellow crystalline solid was diluted with an equal volume of ether, filtered, washed with ether, and air dried. There was obtained the title compound (23.7 g, 85% yield) as a yellow solid, mp 142.5°-146.5° C. Theor. C12 H16 FNO5 S: C, 47.20; H, 5.28; N, 4.59; Found: C, 47.18; H, 5.27; N, 4.49; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1049 g (84%) | With acetic acid In water | 1 N-(2-acetyl-4,5-dimethoxyphenyl)-β-alanine EXAMPLE 1 N-(2-acetyl-4,5-dimethoxyphenyl)-β-alanine A mixture of 2-amino-4,5-dimethoxyacetophenone (910 g, 4.66 mol), acrylic acid (730 ml., 10.67 mol), and acetic acid (2100 ml) was heated at 90° C. for 2 hours. Following treatment with Darco and hot filtration, the product was precipitated by the addition of water (2475 ml) over a 1 hour period. The reaction mixture was cooled and the product was filtered and washed with cold distilled water (4*90 ml) and cold methanol (1*600 ml). Drying under vacuum at 60° C. gave 1049 g (84%) of the product as a yellow powder, mp 149.5°-151.5° C. NMR (CDCl3) δ 2.50 (s, 3H, ArCOCH3), 2.73 (t, 2H, CH2 --CO2 H), 3.57 (t, 2H, N--CH2), 3.82 (s, 3H, CH3 OAr), 3.93 (s, 3H, CH3 OAr), 6.18 (s, 1H, ArH), 7.13 (s, 1H, ArH), 10.05 (broad s, 2H, NH, COOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.2% | With sodium hydrogencarbonate; triethylamine In hexane; dichloromethane | 20 2'-(N-2-Carbethoxyethylamino)-4',5'-dimethoxyacetophenone EXAMPLE 20 2'-(N-2-Carbethoxyethylamino)-4',5'-dimethoxyacetophenone Triethylamine (3.88 g, 5.34 mL, 38.44 mM) was added at once under N2 to a stirred mixture of 2'-amino-4',5'-dimethoxyacetophenone (2.5 g, 12.8 mM) and ethyl 3-bromopropionate (17.43 mL, 96.2 mM) at room temperature. Immediately the reaction mixture solified. This was heated under N2 to 140°-150° C. (bath temp.) for a period of 4 hours during which the reaction mixture had partially liquified into a red-brown, viscous slurry. After cooling to room temperature it was treated with 5% NaHCO3 solution (50 mL) and then extracted with CH2 Cl2 (3*60 mL). The combined organic extracts were washed with H2 O, dried (Na2 SO4) and evaporated in vacuo to remove CH2 Cl2 (low vacuum) and excess 3-bromopropionate (under high vacuum at 50°-60° C.). The dark oily residue was chromatographed on a column of SilicAR CC-7 (300 g, 55.5*6 cm) packed in hexane. The sample was applied to the column in CH2 Cl2 (50 mL) followed by elution with hexane and then with increasing proportions of ethyl acetate/hexane, collecting 1 L fractions. Fractions 10 and 11, afforded, upon evaporation to dryness 2'-(N-2-carbethoxyethylamino)-4',5'-dimethoxyacetophenone as a waxy crystalline solid (1.33 g, 35.2%), mp 73°-75° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran; ethanol | 65 N-Ethyl-N'- {4-[(2-acetyl-4,5-dimethoxyphenyl)aminocarbonylethyl]-phenyl}urea Example 65 N-Ethyl-N'- {4-[(2-acetyl-4,5-dimethoxyphenyl)aminocarbonylethyl]-phenyl}urea 0.60 g of 2-amino-4,5-dimethoxyacetophenone was dissolved in 30 ml of THF. 0.75 g of 4-nitrocinnamoyl chloride and 0.45 g of triethylamine were then added thereto and the mixture was stirred under reflux for 1.5 hours. The solvent of the reaction solution was removed by distillation under reduced pressure. The residue was washed with methanol and then dried. Thus, 1.22 g of yellow solid was obtained. Subsequently, this solid and 90 mg of 5% Pd/C were added to a mixed solvent comprising 100 ml of ethanol and 30 ml of THF and the mixture was stirred under hydrogen atmosphere at room temperature for 32 hours. The reaction solution was filtered and the filtrate was concentrated. Thus, 0.92 g of 2-(4-aminophenyl)carbonylaminoethyl-4,5-dimethoxyacetophenone was obtained as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium nitrite In water at -5 - 75℃; for 5.75h; | 1.1 Step 1[00132] l-(2-Amino-4,5-dimethoxyphenyl)ethanone (15.60 g, 0.07991 mol) was dissolved in concentrated hydrogen chloride in water (555 mL) and water (78 mL). The reaction mixturewas cooled to -5° C (ice/brine) and a solution of sodium nitrite (5.55 g, 0.0804 mol) in water (20 mL) was added over a period of 45min. The reaction mixturewas stirred another 1 h at 0° C and then warmed to 60-75° C for 4 h. The reaction mixturewas then cooled to room temperature using an ice bath and the resulting precipitate was collected via filtration. The solid hydrochloride salt thus obtained was added to approximately 1.0 L of water and then basifed to pH ~12 with sodium hydroxide. The resulting brown solution was neutralized with hydrochloric acid, and the resulting precipitate was collected to provide 12.77 g of 6,7-dimethoxycinnolin-4-ol as a light tan solid (78% yield), which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | To a solution of 2-amino-4,5-dimethoxylacetophenone (4.5 g, 23 mmol) in DME (100 ml_) was added NaOMe (5.0 g, 92 mmol). The reaction was stirred for 30 min after which ethyl formate (8.5 g, 115 mmol) was added and the reaction mixture was stirred for 16 h at rt. Then NaOEt (21% dispersion in oil, 22 g, 69.1 mmol) was <n="48"/>added and the reaction mixture was stirred for an additional 24 h at it Water (1OmL) was then added, and the mixture was stirred for 1 h, then concentrated under reduced pressure. The pH of the resulting aqueous mixture was adjusted to pH 7 using HCI (2N aqueous solution). The resulting precipitated was collected by filtration, and then successively washed with water, ethyl acetate and ethyl ether. The solid was dried under mechanical vacuum give 2.6 g (yield 55 %) of the title compound.1H NMR (400 MHz, DMSO-cfe) delta 10.97 (bs, 1 H), 7.79 (d, 1 H), 7.42 (s, 1 H), 6.96 (s, 1 H), 5.96 (d, 1 H), 3.84 (s, 3 H), 3.81 (s, 3 H); ES-MS m/z 206.2 [M+H]+, LCMS RT (min) 1.21. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.0833333h; Stage #2: pyrrolidine With potassium hydroxide In water at 0℃; for 0.5h; | 1 Method 1. 1-{4,5-Dimethoxy-2-[(E)-pyrrolidin-1-yldiazenyl]phenyl } ethanone. To a 100 mL round bottom flask charged with a magnetic stir bar and l-(2-amino-4,5- dimethoxyphenyl)ethanone (1.23 g, 6.29 mmol) was added water (4 mL). The mixture was cooled to 0° C with an ice bath and concentrated aqueous HCl (1.95 mL) was added to the reaction mixture. With efficient stirring, a solution of sodium nitrite (0.434 g, 6.9 mmol) in water (3 mL) was added to the reaction mixture via Pasteur pipette. The reaction was allowed to stir for 5 minutes at this temperature followed by the slow addition of a solution of pyrrolidine (0.447 g, 6.30 mmol) in 50 mL of 0.4 N aqueous potassium hydroxide. The reaction was allowed to stir at this temperature for 0.5 h before being poured into a separatory funnel and extracted with DCM (2 X 100 mL). The combined organic extract was dried with MgSO4, filtered, and concentrated in vacuo to yield the crude product which was purified on 80 g of silica using hexanes/EtOAc (1:1) as eluent to give 1.49 g (85 %) of the title compound as a brown solid. 1H NMR: 7.12 (s, 1 H), 7.01 (s, 1 H), 3.92 (m, 2 H), 3.80 (s, 3 H), 3.75 (s, 3 H), 3.58 (m, 2 H), 2.60 (s, 3 H), 2.00 (M, 4 H); m/z: 278. |
85% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: pyrrolidine With potassium hydroxide In water at 0℃; for 0.5h; | 1 To a 100 mL round bottom flask charged with a magnetic stir bar and l-(2-amino-4,5- dimethoxyphenyl)ethanone (1.23 g, 6.29 mmol) was added water (4 mL). The mixture was cooled to 0° C with an ice bath and concentrated aqueous HCl (1.95 mL) was added to the reaction mixture. With efficient stirring, a solution of sodium nitrite (0.434 g, 6.9 mmol) in water (3 mL) was added to the reaction mixture via Pasteur pipette. The reaction was allowed to stir for 5 minutes at this temperature followed by the slow addition of a solution of pyrrolidine (0.447 g, 6.30 mmol) in 50 mL of 0.4 N aqueous potassium hydroxide. The reaction was allowed to stir at this temperature for 0.5 h before being poured into a separatory funnel and extracted with DCM (2 x 100 mL). The combined organic extract was dried with MgSO4, filtered, and concentrated in vacuo to yield the crude product which was purified on 80 g of silica using hexanes/EtOAc (1 : 1) as eluent to give 1.49 g (85 %) of the title compound as a brown solid. 1H NMR: 7.12 (s, 1 H), 7.01 (s, 1 H), 3.92 (m, 2 H), 3.80 (s, 3 H), 3.75 (s, 3 H), 3.58 (m, 2 H), 2.60 (s, 3 H), 2.00 (M, 4 H); m/z: 278 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.5% | With ammonium acetate at 165℃; for 10h; Heating / reflux; | 18 [0336] To a IL flask provided with mechanical stirrer, condenser, nitrogen trap and drying tube are added in order: ethyl-cyanoacetate (88.2 g, 83.1 ml, 0.78 mol, 2 eq.), 2- amino-4,5 dimethoxyacetophenone (75 g, 0.390 mol, 1 eq.), and ammonium acetate (15 g, 0.195 mol, 0.5 eq.) under vigorous stirring. The mixture is heated to 165 C° in an oil bath. The reaction mixture is kept under reflux for 10 hours, cooled to room temperature, and diluted with 500 ml cold water. After 1 hour the suspension is filtered, solid precipitate collected, washed 3x 200 ml of water, dried in vacuum oven at 60 C° overnight. The title compound (60.5 g. 64.5%) is obtained as a light yellow solid. MS: m/e 243.3 (M+H)+1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.3% | With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 60℃; Inert atmosphere; | |
58% | With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 60℃; for 1h; Inert atmosphere; | 53.3 Step 3: preparation of 1-(2-amino-dimethoxyphenyl)ethan-1-one oxime 1-(4,5-dimethoxy-2-aminophenyl)ethan-1-one (800mg, 4.1mmol), hydroxylamine hydrochloride (880 mg, 12.3 mmol) and NaOH (1.31 g, 32.8 mmol) were added to 6 mL of ethanol aqueous solution (85%). The reaction solution was heated at 60 °C for 1 hour, concentrated, extracted with ethyl acetate and recrystallized from ethyl acetate-petroleum ether to obtain 1-(2-amino-dimethoxyphenyl)ethan-1-one oxime (500 mg, 58%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With β‐cyclodextrin In water at 65 - 75℃; for 6h; | |
87% | With copper(II) oxide In acetonitrile at 40℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With β‐cyclodextrin In water at 65 - 75℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With cesium fluoride In acetonitrile at 65℃; for 24h; Sealed vial; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper; potassium carbonate In dibutyl ether for 24h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: pyrrolidine With sodium hydroxide In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In dichloromethane at 20℃; Cooling with ice; | 1 General procedure for the preparation of acrylamides 9 General procedure: To a solution of substituted aniline (1.00 mmol) in dichloromethane (2 mL) triethylamine (1.10 mmol) was added. The mixture was cooled in an ice bath and acryloyl chloride (1.05 mmol) was added dropwise. The reaction mixture was stirred for 24 h at room temperature and extracted with water (3 × 3 mL). Subsequently, the inorganic layer was extracted with ethyl ether (3 × 5 mL). The combined organic layers were dried over anhydrous MgSO4 and filtered. After evaporation of solvents the residue was purified on a silica column with chloroform:methanol mixtures (100:1, 50:1 v/v) as eluents to afford the respective acrylamides 9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With zinc trifluoromethanesulfonate In toluene at 110℃; for 8h; | Typical procedure for preparation of quinazoline 3-oxides 2a-2h & 4a-4h: General procedure: Ina 50ml round bottom flask fitted with condenser and calcium chloride guard tubea mixture of 2-aminoacetophenone 1a (500 mg, 3.7mmol), acetohydroxamic acid (332 mg, 4.4 mmol) and 5ml toluene were taken. To this zinc(II) triflate (67 mg, 0.18 mmol) was added and stirred the reaction mixture at 110 °C for 6 hours. After completion of reaction by TLC, the crude mixture was concentrated under vacuum and the crude product was purified by normal column chromatography (silica gel 100-200 mesh, ethyl acetate/hexane = 1:2) to obtain 2,4- dimethylquinazoline 3-oxide 2a as a yellow solid (610 mg, 95%, m.p.101-102 °C) and it was characterized by the following spectral data: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(II) oxide In acetonitrile at 40℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With ammonium acetate In neat (no solvent) at 110℃; for 2h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With ammonium acetate In neat (no solvent) at 110℃; for 2h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 73% 2: 17% | With brij 35 In water at 25℃; Irradiation; Micellar solution; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In methanol Reflux; | General Procedure for the Synthesisof Compounds (I)-(X) General procedure: A mixture of the corresponding 1(2aminophenyl)ethanone (1.5 mmol) and electrophile (1.5 mmol)in MeOH (15 mL) (Fig. 1) was refluxed for 2-3 h. Thehot mixture was filtered via a Büchner funnel. The filtrate was concentrated and the formed solid was filtered off yielding compounds (I)-(VI), (VIII), and (IX). If the solid was formed during the synthesis, itwas combined with that obtained after the concentration of filtrate yielding compounds (VII) and (X). Thecompounds (III), (IV), (VIII), (IX), and (X) were crystallized from MeOH (5 mL); compounds (I), (II), and(VII) from a mixture MeOH/H2O (3 : 1, 5 mL); andcompounds (V) and (VI) from MeOH/H2O (2 : 1, 5 mL). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With iodine; potassium carbonate In dimethyl sulfoxide at 100℃; for 6h; Green chemistry; | General procedure for the synthesis of indoles and pyrroles General procedure: A mixture of 2-amino acetophenone (1 or 4)(1 mmol, 1 eq.), phenyl acetylene (2)(1 mmol, 1 eq.), I2 (1.5 eq.) and K2CO3 (1eq.) in DMSO (4mL) was stirred at 100 C for 6hrs in open air. After completion of the reaction, as indicated by TLC, the solvent was diluted with water and extracted with ethyl acetate (10 x 3 times). After solvent was removed in vacuo. The resulting residue was subjected to column chromatography on silica gel using petroleum ether/ethylacetate as eluent to afford the product 3 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With iodine; potassium carbonate In dimethyl sulfoxide at 100℃; for 6h; Green chemistry; | General procedure for the synthesis of indoles and pyrroles General procedure: A mixture of 2-amino acetophenone (1 or 4)(1 mmol, 1 eq.), phenyl acetylene (2)(1 mmol, 1 eq.), I2 (1.5 eq.) and K2CO3 (1eq.) in DMSO (4mL) was stirred at 100 C for 6hrs in open air. After completion of the reaction, as indicated by TLC, the solvent was diluted with water and extracted with ethyl acetate (10 x 3 times). After solvent was removed in vacuo. The resulting residue was subjected to column chromatography on silica gel using petroleum ether/ethylacetate as eluent to afford the product 3 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With iodine; potassium carbonate In dimethyl sulfoxide at 100℃; for 6h; Green chemistry; | General procedure for the synthesis of indoles and pyrroles General procedure: A mixture of 2-amino acetophenone (1 or 4)(1 mmol, 1 eq.), phenyl acetylene (2)(1 mmol, 1 eq.), I2 (1.5 eq.) and K2CO3 (1eq.) in DMSO (4mL) was stirred at 100 C for 6hrs in open air. After completion of the reaction, as indicated by TLC, the solvent was diluted with water and extracted with ethyl acetate (10 x 3 times). After solvent was removed in vacuo. The resulting residue was subjected to column chromatography on silica gel using petroleum ether/ethylacetate as eluent to afford the product 3 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With iodine; potassium carbonate In dimethyl sulfoxide at 100℃; for 6h; Green chemistry; | General procedure for the synthesis of indoles and pyrroles General procedure: A mixture of 2-amino acetophenone (1 or 4)(1 mmol, 1 eq.), phenyl acetylene (2)(1 mmol, 1 eq.), I2 (1.5 eq.) and K2CO3 (1eq.) in DMSO (4mL) was stirred at 100 C for 6hrs in open air. After completion of the reaction, as indicated by TLC, the solvent was diluted with water and extracted with ethyl acetate (10 x 3 times). After solvent was removed in vacuo. The resulting residue was subjected to column chromatography on silica gel using petroleum ether/ethylacetate as eluent to afford the product 3 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In acetonitrile at 20℃; for 2h; | |
55% | Stage #1: 2-amino-4,5-dimethoxyacetophenone With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 0.0833333h; Stage #2: With potassium iodide In water at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With barium hydroxide octahydrate In methanol at 35℃; for 24h; | (E)-1-(2-Amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (6, C18H19NO4) 1-(2-Amino-4,5-dimethoxyphenyl)ethanone (4.24 mmol)and 4-methoxybenzaldehyde (4.24 mmol) were dissolvedin 10 cm3 of methanol at 35 C under reflux. Subsequently,a solution of 20 cm3 of methanol containing bariumhydroxide octahydrate (16.96 mmol) was added dropwiseto the reaction mixture. The reaction mixture was stirredfor 24 h and the progress was monitored by TLC. Then themixture was concentrated under vacuum, quenched with0.1 M HCl and extracted with ethyl acetate. The organiclayer was separated, dried over Na2SO4 and then concentratedunder vacuum. The reaction mixture was purified byflash column chromatography (hexane/ethyl acetate 9:2) toobtain pure 6. Yield: 40 %; 1H NMR (500 MHz, methanold4):d = 3.82 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 3.86 (s,3H, OCH3), 6.36 (s, 1H, H-60), 6.96-6.98 (d, J = 8.8 Hz,2H, H-2, H-6), 7.39 (s, 1H, H-30), 7.56-7.60 (d, 1H,J = 15.5 Hz, Ha), 7.60-7.63 (d, J = 15.5 Hz, 1H, H-b),7.68-7.67 (d, J = 8.50 Hz, 2H, H-4, H-5) ppm; 13C NMR(126 MHz, methanol-d4): d = 191.6 (C=O), 163.1 (C-40),157.8 (C-50), 151.7 (C-4), 143.3 (C-b), 141.3 (C-10), 131.3(C-5, C-3), 129.6 (C-20), 122.4 (C-a), 115.9 (C-30), 115.7(C-2, C-6), 112.2 (C-1), 100.6 (C-60), 56.4 (C-OCH3), 56.2(C-OCH3), 56.1(C-OCH3) ppm; FT-IR (KBr): m = 3386,3267, 1630, 1563, 1501, 1401, 1342 cm-1; UV/Vis(methanol): kmax = 244, 323, 412 nm; HRMS (ESI-MS): m/z = 336.1206 ([M?Na]?), 314.1384 ([M?H]?, calcd.for C18H19NO4 314.1386). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 2-amino-4,5-dimethoxyacetophenone In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere; | |
76% | Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.666667h; Schlenk technique; Inert atmosphere; Stage #2: 2-amino-4,5-dimethoxyacetophenone In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere; | |
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-amino-4,5-dimethoxyacetophenone In tetrahydrofuran at 20℃; Inert atmosphere; |
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.666667h; Stage #2: 2-amino-4,5-dimethoxyacetophenone In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With indium(III) bromide In chlorobenzene at 110℃; for 24h; Inert atmosphere; Schlenk technique; | I. Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: A GeneralProcedure for Tables 3-5 General procedure: InBr3 [(4.43 mg, 12.5 μmol), (13.3 mg, 37.5 μmol) or (39.0 mg, 110 μmol)] or InI3 (6.19mg, 12.5 μmol) was placed in a 20 mL Schlenk tube, which was heated at 80 °C in vacuo for 15min. The tube was cooled down to room temperature and filled with argon or air. PhCl (0.20,0.30, 0.40, 0.50 or 1.7 mL) or o-C6H4Cl2 (0.20 mL) was added to the tube, and the mixture wasthen stirred at room temperature for 3 min. To this were added alkoxyheteroarenes 3 (0.250,0.300, 0.500, 0.625 or 5.50 mmol) and o-acylanilines 2 (0.250, 0.300 or 2.20 mmol) in the order,and the mixture was stirred at 70, 100, 110, 120, 130 or 170 °C. After stirring for 3, 24 or 36 h,a saturated NaHCO3 aqueous solution (0.5 mL) was added at room temperature, and theresulting mixture was stirred for 20 min. The aqueous phase was extracted with EtOAc (5 mL× 3). The combined organic layer was washed with brine (1 mL) and then dried overanhydrous sodium sulfate (Na2SO4). Filtration and evaporation of the solvent followed bypurification gave product 4. Unless otherwise noted, the annulation reaction was performedaccording to the above procedure, and products 4 synthesized here were fully characterized by1H and 13C NMR spectroscopy and HRMS. Products 4 with fluorine atoms were characterizedadditionally by 19F NMR spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; oxygen; copper(II) nitrate In dimethyl sulfoxide at 130℃; for 26h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49 mg | With pyridine; oxygen; copper(II) nitrate In dimethyl sulfoxide at 130℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethylamine In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(II) bis(trifluoromethanesulfonate) In 1,1,2,2-tetrachloroethane at 100℃; for 14h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In tetrahydrofuran at 20℃; for 2h; | 20 To a solution of 1-(2-amino-4,5-dimethoxyphenyl)ethanone (10 g, 51.2 mmol) in THF (200 mL) was added triethylamine (10.37 g, 102 mmol), and the reaction mixture was stirred. And, acetyl chloride (6.03 g, 77 mmol) was added thereto. After stirring the reaction mixture at room temperature for 2 hours, 10% aqueous potassium hydroxide was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, and then concentrated in vacuo to give Compound (G-1) (12.15 g, 100%). (0932) LC/MS (Condition (3)): [M+H]+/Rt=238/0.65 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 1,4-diaza-bicyclo[2.2.2]octane; sulfur In dimethyl sulfoxide at 120℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With ammonium acetate; dihydrogen peroxide In water; dimethyl sulfoxide at 60℃; for 6h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With ammonium acetate; dihydrogen peroxide In water; dimethyl sulfoxide at 60℃; for 6h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine In tetrahydrofuran at 0 - 20℃; | 4.1.3. General procedure for synthesis of the benzoyl derivatives(11a, b) General procedure: Compound 9 (0.976 g, 5 mmol) was dissolved in dry THF (8 mL)and Et3N (2 mL) and the mixture was cooled in ice bath. Then, a solution of the appropriate benzoyl chloride 10a, b (5.1 mmol) indry THF (2 mL) was added dropwise. After 30 min at 0 C, the reactionmixture was stirred overnight at room temperature. Afterreaction completion, the reaction mixture was poured into icewater (50 mL). The precipitate separated was filtered off, washedseveral times with water then methanol, dried under vacuum andcrystallized from acetone to afford compounds 11a, b as yellowcrystals. 4.1.3.1. N-(2-Acetyl-4,5-dimethoxyphenyl)-4-chlorobenzamide (11a).Yellow solid, yield 81%, m.p. 182e184 C; IR (KBr, y cm1): 3163(NHeC]O), 3084, 3058 (CH aromatic), 2995, 2966, 2953, 2934 (CHaliphatic), 1720 (CH3C]O), 1667 (NHeC]O), 1595 (C]C aromatic);1H NMR (400 MHz, CDCl3) d (ppm): 2.66 (s, 3H, CH3), 3.92 (s, 3H,OCH3), 4.02 (s, 3H, OCH3), 7.31 (s, 1H, phenyl CH), 7.48 (d, 2H,benzoyl 2CH, J 8.6 Hz), 7.99 (d, 2H, benzoyl 2CH, J 8.6 Hz), 8.71(s, 1H, phenyl CH), 13.01 (s, 1H, NH); 13C NMR (100 MHz, CDCl3)d (ppm): 28.50, 56.37, 56.49, 103.56, 113.89, 114.64, 128.95, 129.17,133.28, 138.21, 138.40, 143.91, 155, 165.07 (C]O), 201.35 (C]O);HRESIMS (m/z): [MNa] Calcd for C17H16ClNO4Na, 356.06601;found, 356.06613. |
With triethylamine In tetrahydrofuran at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In tetrahydrofuran at 0 - 20℃; | 4.1.3. General procedure for synthesis of the benzoyl derivatives(11a, b) General procedure: Compound 9 (0.976 g, 5 mmol) was dissolved in dry THF (8 mL)and Et3N (2 mL) and the mixture was cooled in ice bath. Then, a solution of the appropriate benzoyl chloride 10a, b (5.1 mmol) indry THF (2 mL) was added dropwise. After 30 min at 0 C, the reactionmixture was stirred overnight at room temperature. Afterreaction completion, the reaction mixture was poured into icewater (50 mL). The precipitate separated was filtered off, washedseveral times with water then methanol, dried under vacuum andcrystallized from acetone to afford compounds 11a, b as yellowcrystals. |
With triethylamine In tetrahydrofuran at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triethylamine In tetrahydrofuran at 0 - 20℃; | 4.1.3. General procedure for synthesis of the benzoyl derivatives(11a, b) General procedure: Compound 9 (0.976 g, 5 mmol) was dissolved in dry THF (8 mL)and Et3N (2 mL) and the mixture was cooled in ice bath. Then, a solution of the appropriate benzoyl chloride 10a, b (5.1 mmol) indry THF (2 mL) was added dropwise. After 30 min at 0 C, the reactionmixture was stirred overnight at room temperature. Afterreaction completion, the reaction mixture was poured into icewater (50 mL). The precipitate separated was filtered off, washedseveral times with water then methanol, dried under vacuum andcrystallized from acetone to afford compounds 11a, b as yellowcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triethylamine In tetrahydrofuran at 0 - 20℃; | 4.1.3. General procedure for synthesis of the benzoyl derivatives(11a, b) General procedure: Compound 9 (0.976 g, 5 mmol) was dissolved in dry THF (8 mL)and Et3N (2 mL) and the mixture was cooled in ice bath. Then, a solution of the appropriate benzoyl chloride 10a, b (5.1 mmol) indry THF (2 mL) was added dropwise. After 30 min at 0 C, the reactionmixture was stirred overnight at room temperature. Afterreaction completion, the reaction mixture was poured into icewater (50 mL). The precipitate separated was filtered off, washedseveral times with water then methanol, dried under vacuum andcrystallized from acetone to afford compounds 11a, b as yellowcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine In tetrahydrofuran at 0 - 20℃; | 4.1.3. General procedure for synthesis of the benzoyl derivatives(11a, b) General procedure: Compound 9 (0.976 g, 5 mmol) was dissolved in dry THF (8 mL)and Et3N (2 mL) and the mixture was cooled in ice bath. Then, a solution of the appropriate benzoyl chloride 10a, b (5.1 mmol) indry THF (2 mL) was added dropwise. After 30 min at 0 C, the reactionmixture was stirred overnight at room temperature. Afterreaction completion, the reaction mixture was poured into icewater (50 mL). The precipitate separated was filtered off, washedseveral times with water then methanol, dried under vacuum andcrystallized from acetone to afford compounds 11a, b as yellowcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper(l) iodide In acetonitrile at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In tetrahydrofuran at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With hydrogenchloride; NaNO2 In lithium hydroxide monohydrate at 0 - 75℃; for 5h; | 27.1 Step-1: Synthesis of 6,7-dimethoxycinnolin-4(1H)-one: To a solution of 1-(2- amino-4,5-dimethoxyphenyl)ethanone (1 g, 5.12 mmol, 1 eq) in a solution of Conc.HCl (36 mL) and water (5 mL) at 0 °C was added a solution of sodium nitrite (0.353 g, 5.12 mmol, 1 eq) in water (2 mL) dropwise. The mixture was allowed to stir at 0 °C for 1 h followed by stirring at 75 °C for 4 h. Progress of reaction was monitored by 1H NMR. After completion, reaction mixture was cooled to RT, precipitates was filtered, dissolved in water (150 mL) and basified with aq. NaOH up to pH 12 and then neutralized with 2M HCl solution. Precipitate was filtered, washed with hexane and dried under vacuum to afford 6,7-dimethoxycinnolin- 4(1H)-one (0.6 g, 57%). LCMS: 207 [M+1]+ |
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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