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CAS No. : | 287119-84-0 | MDL No. : | MFCD11846173 |
Formula : | C10H11NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 209.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
98% | at 20℃; for 15 h; | Step 3: methyl 2-(2-methyl-5-nitrophenyl)acetate Ex.4b was dissolved in ethanol (60 mL). To this solution was added a spatula of 10percent palladium on carbon. After that the mixture was degassed, a balloon filled with hydrogen was fitted. The reaction was stirred at rt for 15h. The reaction was monitored by TLC. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and dried at high vacuum to afford methyl 2-(5-amino-2-methylphenyl)acetate (3.61 g, 98percent) in a high purity grade. No further purification was needed. |
96% | at 20℃; for 2 h; | Step 3: methyl 2-(2-methyl-5-nitrophenyl)acetate Ex.3b (2.55 g, 12.19 mmol) was dissolved in ethanol (60 mL). To this solution was added 10percent palladium on carbon (ca 260 mg). The mixture was degassed with N2 and a balloon filled with hydrogen was fitted. The reaction was stirred at rt for 2h. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and dried under high vacuum to afford the desired product in a high purity grade (2.10 g, 96percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With thionyl chloride; at 0 - 85℃; for 3h; | Compound 1-2 (20.0 g, 102 mmol)Was dissolved in methanol (250 mL)0 ~ 5 the following was slowly added thionyl chloride (27.5g, 204mmol),Maintaining the temperature at 75 ~ 85 reaction 3 hours;After the reaction is cooled to room temperature,Add water plus ethyl acetate extraction,The organic phase was washed twice with sodium bicarbonate,Dried over anhydrous sodium sulfate, concentrated,Compound 1-3 (21.0 g) was obtained in a yield of 98.0%. |
95% | With hydrogenchloride; In 1,4-dioxane; for 2h; | Step 2: hydrochloric acid solution (10.8 mL, 43.12 mmol) was added to a solution of <strong>[287119-83-9]2-<strong>[287119-83-9](2-methyl-5-nitrophenyl)acetic acid</strong></strong> Ex.4a (4.21 g, 21.56 mmol) in methanol. The reaction mixture was refluxed for 2h. LCMS showed the formation of theexpected product as the only peak. After cooling to rt and removing the solvent in vacuo, the crude product was dissolved in water and basified to pH>12 using 2N NaOH. The solution was extracted using EtOAc and the combined organic layer were washed with brine, dried, filtered and the solution was concentrated under reduced pressure. The resulting solid methyl 2-(2-methyl-5-n itrophenyl )acetate (4.31 g, 95%) was used as such in the next synthetic step. |
23% | With hydrogenchloride; In 1,4-dioxane; at 65℃; for 15h; | - Step 2: 4 M HCI in dioxane (26.6 mL, 106.46 mmol)) was added to a solution of previously synthesized nitro derivative Ex.3a (10.39 g, 53.23 mmol) in methanol (150 mL). The reaction mixture was refluxed for 1 5h. After cooling to rt and removing the excess of solvent under reduced pressure, the crude product was dissolved in water and basified to pH>12 using 2N NaOH. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over Mg504, filtered and the solution was concentrated to reduced pressure. The residue was purified by flash chromatography on silica gel eluting with heptanes and EtOAc to afford methyl 2-(2-methyl-5-nitrophenyl)acetate Ex.3b (2.55 g, 23%). |
With hydrogenchloride; In 1,4-dioxane; for 14h;Heating / reflux; | <strong>[287119-83-9]2-(2-Methyl-5-nitrophenyl)acetic acid</strong> 13 (30 g, 154 mmol) is dissolved in methanol (700 mL) and HCl (79 mL of a 4 M solution in 1,4-dioxane, 316 mmol) is added. The reaction is heated to reflux for 14 h. After cooling to rt and removing solvent in vacuo, the crude product is dissolved in water (500 mL) and basified to pH > 12 using 2N sodium hydroxide. The solution is extracted using ethyl acetate and the combined organic layer is washed with brine, dried over sodium sulfate and filtered. After removing the solvent in vacuo, the product 14 is obtained as a dark yellow solid. 1H NMR (300MHz, CDCl3) delta 8.06 (m, 2H), 7.33 (d, J= 8.4 Hz, IH), 3.73 (s, 3H), 3.72 (s, 2H), 2.41 (s, 3H). | |
[00125] <strong>[287119-83-9]2-(2-Methyl-5-nitrophenyl)acetic acid</strong> 13 (30 g, 154 mmol) was dissolved in methanol (700 mL) and HCl (79 mL of a 4 M solution in 1,4-dioxane, 316 mmol) was added. The reaction was heated to reflux for 14 h. After cooling to rt and removing solvent in vacuo, the crude product was dissolved in of water (500 mL) and basified to pH > 12 using 2N sodium hydroxide. The solution was extracted using ethyl acetate and the combined organic layer was washed with brine, dried over sodium sulfate and filtered. After removing the solvent in vacuo, the product 14 was obtained as a dark yellow solid. 1H NMR (300MHz, CDCl3) delta 8.06 (m, 2H), 7.33 (d, J= 8.4 Hz, IH), 3.73 (s, 3H), 3.72 (s, 2H), 2.41 (s, 3H). | ||
With hydrogenchloride; In 1,4-dioxane; for 14h;Heating / reflux; | 2- (2-methyl-5-nitrophenyl)-acetic acid (1.9g, 9. 7mmol) is dissolved in 50mL methanol and 5mL 4M HC1 in 1,4-dioxane is added. The reaction is heated to reflux for 14 hours. After cooling down and removing solvent, the crude product is dissolved in 50mL water and basified by 2N sodium hydroxide water solution to pH>12. The solution is extracted by ethyl acetate, and the combined organic layer is washed by brine and dried over sodium sulfate and filtered. After removing solvent, the final product compound (16) 2- (2- methyl-5-nitrophenyl)-acetic acid methyl ester is the dark yellow solid, 1.85g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With palladium 10% on activated carbon; hydrogen; at 20℃; for 15.0h; | Step 3: methyl 2-(2-methyl-5-nitrophenyl)acetate Ex.4b was dissolved in ethanol (60 mL). To this solution was added a spatula of 10% palladium on carbon. After that the mixture was degassed, a balloon filled with hydrogen was fitted. The reaction was stirred at rt for 15h. The reaction was monitored by TLC. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and dried at high vacuum to afford methyl 2-(5-amino-2-methylphenyl)acetate (3.61 g, 98%) in a high purity grade. No further purification was needed. |
96% | With palladium 10% on activated carbon; hydrogen; at 20℃; for 2.0h; | Step 3: methyl 2-(2-methyl-5-nitrophenyl)acetate Ex.3b (2.55 g, 12.19 mmol) was dissolved in ethanol (60 mL). To this solution was added 10% palladium on carbon (ca 260 mg). The mixture was degassed with N2 and a balloon filled with hydrogen was fitted. The reaction was stirred at rt for 2h. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and dried under high vacuum to afford the desired product in a high purity grade (2.10 g, 96%). |
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 16.0h; | 2-(2-Methyl-5-nitrophenyl)acetic acid methyl ester 14 (32 g, 153 mmol) is dissolved in ethanol (750 mL). To this solution is added 10% palladium on carbon (3.2 g). After purging the reaction flask of oxygen, a balloon filled with hydrogen is fitted. The reaction is stirred at rt for 16 h. After removing the catalyst by filtering through a celite plug and removing the solvent in vacuo, the crude product is purified using flash chromatography (ethyl acetate : petroleum ether = 5 : 1). The product 7 is isolated as a yellow oil. 1H NMR (300MHz, CDCl3) delta 6.9 (d, J= 7.8 Hz), 6.59 (m, IH), 6.56 (m, IH), 3.69 (s, 3H). |
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 16.0h; | [00126] 2-(2-Methyl-5-nitrophenyl)acetic acid methyl ester 14 (32 g, 153 mmol) was dissolved in ethanol (750 mL). To this solution was added 10% palladium on carbon (3.2 g). After the mixture was degassed, a balloon filled with hydrogen was fitted. The reaction was stirred at rt for 16 h. After removing the catalyst by filtering through a celite plug and removing the solvent in vacuo, the crude product was purified using flash chromatography (ethyl acetate : petroleum ether = 5 : 1). The product 7 was isolated as a yellow oil. 1H NMR (300MHz, CDCl3) delta 6.9 (d, J= 7.8 Hz), 6.59 (m, IH), 6.56 (m, IH), 3.69 (s, 3H). | |
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 16.0h; | 2- (2-methyl-5-nitrophenyl)-acetic acid methyl ester (1.85g, 8. 85mmol) is dissolved in 40mL ethanol. 180mg 10% palladium carbon is added and a hydrogen balloon is used. The reaction is stirred in RT for 16 hours. After removing the palladium carbon by going through a celite plug and removing the solvent, the crude product is purified by flash chromatography using MeOH/DCM (7%: 93%). The final product compound (7) 2- (5- amino-2-methyl-phenyl) -acetic acid methyl ester is the yellow oil, 1. 5g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h; | 3. 4-Benzyl-9-methyl-7-(2-methyl-5-nitro-phenyl)-4,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one A mixture of 7-benzyl-4-methylamino-7H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (400 mg, 1.5 mmol), <strong>[287119-84-0](2-methyl-5-nitro-phenyl)-acetic acid methyl ester</strong> (350 mg, 1.67 mmol) and cesium carbonate (1.1 g, 3 mmol) in 5 ml anhydrous DMF is heated to 120 C. for 30 min. The reaction mixture is cooled down to room temperature. The reaction mixture is partitioned in water and ethyl acetate, extracted with ethyl acetate three times. The organic phase is combined and washed with brine, dried over Na2SO4. The crude product is purified by silica gel flash chromatography, eluted with 40% to 100% ethyl acetate in hexane to give the title compound as light yellow solid. MS m/z 426.2 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.8% | In the ice bath conditions,Compounds 1-3 (10.0 g, 47.8 mmol)Was dissolved in N, N-dimethylformamide (i.e., DMF, 100 mL)Sodium hydride (3.8 g, 95.6 mmol) was slowly addedTo the reaction system at 0 C for 15 minutes;1,2-dibromoethane (26.0 g, 143.4 mmol)Dropping into the reaction system,Heated to 45 C for 3 hours;Cooled and poured into 50 mL of water,Extracted with ethyl acetate, dried,Concentrated, silica gel column chromatography,Compound 1-4 (2.0 g) was obtained in a yield of 17.8%. |
Tags: 287119-84-0 synthesis path| 287119-84-0 SDS| 287119-84-0 COA| 287119-84-0 purity| 287119-84-0 application| 287119-84-0 NMR| 287119-84-0 COA| 287119-84-0 structure
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