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CAS No. : | 7712-28-9 | MDL No. : | MFCD01820403 |
Formula : | C11H10N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HROJWOXFEZYMGL-UHFFFAOYSA-N |
M.W : | 218.21 | Pubchem ID : | 151480 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In ethanol; for 0.1h;Microwave irradiation; | To a solution of 1.1g (10 mmoles) of o-fenilendiamina in ethanol (5 mL) in a microwave reaction tube was -ketoglutaric acid (1.5g; 10.30 mmol). The reaction mixture was irradiated with MW during 1 min. at 30 W followed by 5 min at 15 W. The crude product was filtered, washed with NaOH 5% and water. Compound 10 was obtained as a white solid (2.10, 98%) crystallized from ethanol; mp: 256-258 C; mp lit.: 257-258 C [2a,3]. IR (Film): 3435, 3102, 1730, 1666, 1608, 1502 cm-1.1H-NMR (300 MHz, DMSO-d6): 2.72 (t; J=6.30 Hz; 2H; CH2); 3.02 (t; J=6.30 Hz; 2H; CH2); 7.21-7.35 (m; 2H; ArH); 7.46 (t; J= 7.65 Hz; 1H; ArH), 7.69 (d; J= 8.06, 1H, ArH), 12.10 (bs; 1H; OH); 12.30 (bs; 1H; OH) ppm. 13C-NMR (75 MHz,DMSO-d6): delta 28.1; 30.4; 115.7; 123.5; 128.5; 129.9; 131.9, 132.1; 155.0 (C=N); 160.7; 174.4 (COOH) ppm. MS (m/z): 218.1. |
98% | In ethanol; for 0.0833333h;Microwave irradiation; | General procedure: In a typical reaction, o-phenyldiamine (10mmol) and the corresponding dicarbonylic compound (10mmol) were dissolved in ethanol (5ml) in a reaction glass tube equipped with a screw cap and magnetic agitation. The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300 reactor) at 30W for around 5-13min. After cooling, 10ml of ethanol was added to the reaction vessel. The product was recrystallized from ethanol, precipitating as a white solid. |
95.7% | In ethanol; at 20.0℃; for 1h; | Weigh o-phenylenediamine (10.81 g, 0.10 mol),Add 250ml of absolute ethanol,After stirring at room temperature for 15 min to dissolve, 2-oxoglutaric acid (16.11 g, 0.10 mol) was added, which was formed as a milky white solid, stirring was continued for 1 h, and the reaction was completed. Filtering,A white solid was obtained, which was crystallized from ethanol to give 2-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoic acid (Compound 1) 20.73 g.95.7% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With alumina methanesulfonic acid; at 120.0℃; for 0.166667h;Microwave irradiation; | General procedure: In a typical reaction, AMA 2:3 (10mmol), the corresponding carboxylic acid (1mmol) and the alcohol (2ml) were mixed in the provided reaction glass tube equipped with a screw cap and magnetic agitation until a wet mixture was achieved. The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300 reactor) at 120C for 10-25min. On cooling, the mixture was diluted with DCM (41mL), and filtered over celite. Then the filtrate was washed with Na2CO3 (ss) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the ester. |
82.2% | With sulfuric acid; at 78.0℃; | Intermediate 1 (1.75 g, 8 mmol) was dissolved in 25 ml of ethanol, 0.1 ml of concentrated sulfuric acid was added, and refluxed at 78 C.At night, TLC detected that the reaction was completed. The reaction was quenched with ice water and the reaction was completely precipitated and neutralized with NaHCO3 to pH = 7.The mixture was filtered under EtOAc (EtOAc)EtOAc.PE/EA = 10/1 to 5/1 column chromatography, yielding 1.62 g of Compound 2 pure product, yield 82.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With alumina methanesulfonic acid; at 120.0℃; for 0.166667h;Microwave irradiation; | In a typical reaction, AMA 2:3 (10mmol), the corresponding carboxylic acid (1mmol) and the alcohol (2ml) were mixed in the provided reaction glass tube equipped with a screw cap and magnetic agitation until a wet mixture was achieved. The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300 reactor) at 120C for 10-25min. On cooling, the mixture was diluted with DCM (41mL), and filtered over celite. Then the filtrate was washed with Na2CO3 (ss) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the ester. 4.3.6.1 Methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate (23) (0075) Alcohol: Methanol. Reaction time: 10min. Yield: 95%. Mp: 208-209C. IR (cm-1): 1730, 1655, 1615, 1510, 1490, 1565. MS (m/z): 232.3. 1H-RMN (300MHz) delta (ppm) (DMSO-d6): 2.79 (t; J=7.01Hz; 2H; CH2); 3.06 (t; J=6.83Hz; 2H; CH2); 3.60 (s; 3H; OCH3); 7.23-7.33 (m; 2H; ArH); 7.48 (t; J=7.99Hz; 1H; ArH), 7.68 (d; J=8.40; 1H; ArH), 12.36 (s.a.; 1H; NH).13C-RMN (75MHz) delta (ppm) (DMSO-d6): 28.0 (CH2); 29.8 (CH2); 51.8 (OCH3); 115.7; 123.6; 128.6; 130.0; 131.9; 132.2; 155.0 (C=N); 160.4 (C=O); 173.4 (CO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With alumina methanesulfonic acid; at 120.0℃; for 0.166667h;Microwave irradiation; | General procedure: In a typical reaction, AMA 2:3 (10mmol), the corresponding carboxylic acid (1mmol) and the alcohol (2ml) were mixed in the provided reaction glass tube equipped with a screw cap and magnetic agitation until a wet mixture was achieved. The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300 reactor) at 120C for 10-25min. On cooling, the mixture was diluted with DCM (41mL), and filtered over celite. Then the filtrate was washed with Na2CO3 (ss) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the ester. |
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