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CAS No. : | 91-52-1 | MDL No. : | MFCD00002434 |
Formula : | C9H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GPVDHNVGGIAOQT-UHFFFAOYSA-N |
M.W : | 182.17 | Pubchem ID : | 7052 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.39 |
TPSA : | 55.76 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.63 cm/s |
Log Po/w (iLOGP) : | 1.51 |
Log Po/w (XLOGP3) : | 1.1 |
Log Po/w (WLOGP) : | 1.4 |
Log Po/w (MLOGP) : | 1.06 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 1.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.81 |
Solubility : | 2.85 mg/ml ; 0.0156 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.86 |
Solubility : | 2.49 mg/ml ; 0.0137 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.03 |
Solubility : | 1.72 mg/ml ; 0.00942 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.49 |
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 |
---|---|---|
17% | With silver carbonate; copper(ll) bromide; palladium dichloride In tetrahydrofuran at 110℃; for 24 h; | General procedure: A mixture of carboxylic acid (1 equiv., 0.5 mmol), CuBr2 or CuCl2 (2 equiv., 1 mmol), Ag2CO3 (1 equiv., 0.5 mmol) and PdCl2 (0.1 equiv.) was heated inTHF (3 mL) under reflux at 110 oC for 24 h. After the reaction finished, the mixture was evaporated under vacuum and purified by columnchromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sulfuric acid for 3h; Heating; | |
With sulfuric acid | ||
Stage #1: ethanol With thionyl chloride for 0.166667h; Stage #2: 2,4 dimethoxybenzoic acid at 20℃; | 7.1 Synthesis of compound represented by Chemical Formula 49-a 100 ml of ethanol was cooled to 0, 7 ml of thionyl chloride was slowly added dropwise, and the mixture was stirred for 10 minutes. 10 g (0.05 mole) of the compound represented by Reaction 1 was dissolved in ethanol, and the mixture was slowly added dropwise, followed by stirring at room temperature. The product was concentrated under reduced pressure and then dried to obtain a compound represented by [Chemical Formula 49-a]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium hydroxide | |
Stage #1: methyl 2, 4-dimethoxybenzoate With sodium hydroxide; water In ethanol at 25 - 40℃; for 2h; Stage #2: With hydrogenchloride In ethanol; chloroform; water | 10 Reference Example 10 53 g of methyl 2,4-dimethoxybenzoate was dissolved in 160 ML of ethanol, to which 104 ML of a 5M aqueous solution of sodium hydroxide was added, and this mixture was stirred for 2 hours at 25 to 40°C. Then, chloroform and water were added to the reaction mixture, which was adjusted to PH 2 with 6M hydrochloric acid, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 45 g of 2,4-dimethoxybenzoic acid as white solid. NMR(90MHz,CDCl3) δ value: 3.88(3H,s), 4.04(3H,s), 6.53-6.69(2H,m), 8.11(1H,d,J=8.5Hz), 10.34(1H,br) | |
Stage #1: methyl 2, 4-dimethoxybenzoate In water Reflux; Stage #2: With hydrogenchloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 0.5h;Inert atmosphere; | Anhydrous DMF (8 muL, 0.1 mmol) was added to anhydrous DCM (7 mL). Acid 9b (1.00 g, 5.49 mmol) was added and the mixture was cooled to 0C. Oxalylchloride (1.0 mL, 11.7 mmol) was added dropwise and the resulting solution was allowed to warm to r.t. (ca. 30 min.), after which it was concentrated in vacuo and dried. The product was a white solid (1.06 g, 96 %) and was used without purification. [2] |
94.2% | With thionyl chloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20℃; for 8.5h; | Add 1821 mg of 2,4-dimethoxybenzoic acid to the reactor.Add 40 ml of tetrahydrofuran and stir.0.5 ml of N,N-dimethylformamide was added at room temperature, and then stirred at room temperature for 0.5 hour.3 g of thionyl chloride was added dropwise, followed by stirring at room temperature for 8 hours.After the reaction is completed, after the post-treatment and purification process,The compound 2,4-dimethoxybenzoyl chloride was obtained in a yield of 94.2%. |
With thionyl chloride; for 2h;Heating / reflux; | Example 204B 2,4-dimethoxybenzoyl chloride A solution of 2,4-dimethoxybenzoic acid (0.25 g, 1.4 mmol) in 5 mL of SOCl2 was warmed to reflux and was allowed to stir for 2 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude material was diluted with 5 mL of toluene and concentrated under reduced pressure. This dilution with toluene and concentration was repeated two additional times to give the crude title compound which was used without additional purification or characterization. |
With thionyl chloride; for 2h;Heating / reflux; | A solution of 2,4-dimethoxybenzoic acid (0.25 g, 1.4 mmol) in 5 mL of SOCl2 was warmed to reflux and was allowed to stir for 2 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude material was diluted with 5 mL of toluene and concentrated under reduced pressure. This dilution with toluene and concentration was repeated two additional times to give the crude title compound which was used without additional purification or characterization | |
With oxalyl dichloride; In benzene; at 20℃; for 2h; | General procedure: 2-Methoxybenzoic acid (2.0 g, 13.14 mmol) in anhydrous benzene (60 mL) was treated with 5.0 mL of oxalyl chloride and thoroughly stirred at room temperature. After 2 h, the solvent and the excess reagent were removed under reduced pressure. The residue, 2-methoxybenzoyl chloride was dissolved in anhydrous ether (80 mL), 1,3-dimethoxybenzene (1.8 g, 13.03 mmol) and AlCl3 (5.0 g) were added. After stirring for 8 h at room temperature, the mixture was hydrolyzed with ice-cold water (500 mL) containing concentrated HCl (45 mL) and extracted with CHCl3. Solvent removal and purification with gel-column chromatography (CHCl3) gave yellow oil, 2-hydroxy-4-methoxy-2'-methoxybenzophenone and 2,4-dimethoxy-2'-hydroxybenzophenone (2.20 g, 8.53 mmol, 65%). The yellow oil (2.20 g, 8.53 mmol) was treated with pyridine (100 mL), H2O (50 mL) and aqueous 10% tetramethylammonium hydroxide (45 mL). The mixture was refluxed for 36 h, poured into ice, acidified with HCl, and extracted with ether. Purification with gel-chromatography (CHCl3) and recrystallization (CHCl3) gave colorless needle crystals, 3-methoxyxanthone (1.60 g, 7.08 mmol, 83%). A mixture of 3-methoxyxanthone (1.60 g, 7.08 mmol), phenol (42 mL) and HI (35 mL) was refluxed at 160 C for 8 h, and the reaction mixture was poured into aqueous NaHSO3 solution. The resulting yellow precipitate was collected, purified by silica gel-column chromatography (CHCl3:CH3OH) and recrystallized from CH3OH to yield yellow needle crystals, 3-hydroxyxanthone (1.40 g, 6.0 mmol). 3-Hydroxyxanthone was reacted with dibromopropane (1.21 g, 6.0 mmol) to give 1, 3-(3-bromopropoxy)xanthone. Compound 1 was then refluxed with ethanol and corresponding amines to yield 2-6. <strong>[91-52-1]2,4-Dimethoxybenzoic acid</strong> was treated as the procedure mentioned above to yield 3-(3-bromopropoxy)-6-hydroxyxanthone (7) and 3,6-di(3-bromopropoxy)xanthone. Compound 7 was then refluxed with ethanol and corresponding amines to yield 8-14. | |
With oxalyl dichloride; In dichloromethane; at 20℃; for 24h; | General procedure: To a solution of dimethoxylbenzoic acid (2.39 g, 13.14 mmol) in dry dichlormethane (60 mL) was added oxalyl chloride (5.73 mL, 65.7 mmol). The mixture was stirred at room temperature for 24 h and then concentrated under reduced pressure to afford dimethoxylbenzoyl chloride 3a-d as colorless residue. To a solution of 3a-d and 1,2,3-trimethoxybenzene (2, 2.43 g, 14.45 mmol) in 20 mL anhydrous ether, aluminum trichloride (5.26 g, 39.42 mmol) was added at 0 C. The resulting mixture was stirred for 12 h at room temperature under N2 protection. Then a mixture of 15% hydrochloric acid and ethyl acetate (100 mL, V/V = 1:1) were added. The ethyl acetate layer was partitioned, washed with brine (30 mL × 3), dried over magnesium sulfate and concentrated under reduced pressure. The residue was suspended in a solution that contained methanol (22.4 mL), water (14.9 mL) and sodium hydrate (4.9 g, 0.12 mol) at 0 C. Then the reaction mixture was heated to 110 C for next 36 h. After cooled to 0 C, the mixture was acidified with 2 mol/L HCl solution till pH = 2-3. The precipitation was formed, filtered, washed with cold water and dried to provide 4a-d, respectively. | |
With oxalyl dichloride; In dichloromethane; at 20℃; for 4h; | In preparation of 3-hydroxyl-4,6-dimethoxy-9H-xanthenone, 2.4 g (13.14 mmol) of <strong>[91-52-1]2,4-dimethoxy benzoic</strong> acid is dissolved in 60 mL of dried dichloromethane, 5 mL of oxalyl chloride is added, and the said mixture is stirred at room temperature for 24 hours. Once the solvent is evaporated, 80 mL of ethyl ether is added to dissolve resulting residue; 2.19 g (13.03 mmol) of 1,2,3-trimethoxy benzene is added; the said mixture is cooled in an ice-bath for 30 min, 5.0 g of anhydrate AlCl3 (37.5 mmol) is added; the said mixture reacts at room temperature for 12 hours; and the over amount of AlCl3 is quenched with the aid of diluted HCl solution (15%). The obtained is then extracted with ethyl acetate (80 mL*2) and dried with anhydrous sodium sulfate. The resulting residue is condensed in reduced pressure and is directly dissolved in the mixed solution containing methanol (20 mL) and 30% NaOH (40 mL). The said mixture is heated and refluxed for 14 hours, the pH value of the obtained solution is adjusted with the aid of 6 mol/L HCl until the pH value reaches 6, the said mixture is vacuum filtered and dried, and as a result, 3 g of crude product is obtained, and the yield is 81%; m.p. is 120.2 C.-121.2 C.; 1H-NMR (300 MHz, CD3COCD3): 3.98-4.03 (m, 9H), 7.00 (dd, 1H, J1=8.9 Hz, J2=2.4 Hz), 7.09 (d, 1H, J=2.4 Hz), 7.19 (d, 1H, J=9.0 Hz), 7.95 (d, 1H, J=9.0 Hz), 8.13 (d, 1H, J=8.9 Hz); EI-MS (m/z): 286 [M+], 271, 256, 241. | |
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20℃;Inert atmosphere; | General procedure: To a solution of carboxylic acids (1.7 mmol) in dry DMF (100 muL) and dry toluene (15 mL) under nitrogen atmosphere, freshly distillated thionyl chloride (3.4 mmol) was added and the solution was stirred at room temperature overnight. The solvent and thionyl chloride were removed under vacuum. The acid chloride was dissolved with dichloromethane (15 mL) under nitrogen atmosphere and directly used for the synthesis of the boronic acid. | |
With thionyl chloride; for 3h;Inert atmosphere; Reflux; | General procedure: The substituted N,N-diethyl benzamides were prepared from the respective substituted benzoic acids. The acid (5 g, 32.9 mmol) was refluxed with excess thionyl chloride (50 mL) until the evolution of hydrogen chloride was ceased. The excess thionyl chloride was removed under reduced pressure and co-distilled with toluene (3x15 mL). The acid chloride was dissolved in dry CH2Cl2 (100 mL) and added drop wise diethylamine (13.6 mL, 131.5 mmol) at 0 C and stirred at room temperature for overnight. The reaction mixture was diluted with CH2Cl2 (100 mL), washed with water (50 mL), brine solution and dried over anhydrous MgSO4. The organic layer was removed on rotovapor to give the crude compound. The crude compound was purified by flash column chromatography to obtain the pure diethylbenzamide. | |
With thionyl chloride; at 75℃; for 6h;Inert atmosphere; | General procedure: The mixture of suitable substituted benzoic acid (5a-5d, 0.01 mol) and thionyl chloride (5 ml) was stirred at 75 C for 6 h under nitrogen. After removal of excess thionyl chloride in vacuo, 4-methoxy-2-nitroaniline (1b, 0.01 mol) and anhydrous Na2CO3 (0.1 mol) were added to the reaction mixture dissolved in anhydrous acetone (50 ml). After stirring at 54 C for 1 h, the solvent was removed under vacuum and the residue was poured into ice water with stirring. The precipitated solid was fitered, washed with ice water and dried to obtain the corresponding N-phenylbenzamide derivatives (7a-7d). To a solution of N-phenylbenzamide derivatives (7a-7d, 0.01 mol) in anhydrous acetic acid (50 ml) was added iron powder (0.03 mol), and then the mixture was refluxed at 100 C. After completion of the reaction as indicated by TLC, the solvent was evaporated under reduced pressure and the residue was extracted with CH2Cl2 (3 × 20 mL). The combined organic fractions were washed with saturated NaHCO3, brine, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using petroleum ether/EtOAc (10:1-4:1). | |
With thionyl chloride; | To a cooled (ice bath) solution of 6 (0.238 g, 0.81 mmol) in THF (10 mL), NaH (60%, 65 mg, 1.62 mmol) was added. After stirring at 0 C for 15 min, the mixture was added 2,4-dimethoxybenzoyl chloride [prepared from (0.222 g, 1.22 mmol) of 2,4-dimethoxybenzoic acid with 5 mL SOCl2], and refluxed for 30 min. After the acylation was complete, the reaction was cooled to room temperature, poured into ice water (40 mL), and extracted with EtOAc (340 mL). The organic phase was washed with brine, dried over MgSO4 and evaporated, and the residue was chromatographed over silica gel. | |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h; | To a 100mL flask with a CaCl2 tube was added 2,4-dimethoxybenzoicacid S1 (5g, 27.5 mmol) and 20 mL of dry DCM. Oxalyl chloride (4.6mL55mmol) and five drop of DMF were added. The suspension was stirred at r.t. for1h. The solvent was evaporated to give 2,4-dimethoxybenzoyl chloride as an oil. This oil wasdissolved in DCM (10 mL) and was added dropwise to methanol (30 mL). After the addition,the mixture was allowed to stir at r.t. overnight. The solvent was evaporatedand the slurry was dissolved in DCM. The organic solvent was washed with sat.NaHCO3,brine and dried over anhydrous Na2SO4. The solvent was removed by rotaryevaporation to give theproduct methyl 2,4-dimethoxybenzoate S2 asa colourlessoil(5.12 g , 95%).1H NMR (400 MHz, Chloroform-d)delta 7.82 (d, J = 9.4 Hz, 1H), 6.48-6.44 (m, 2H), 3.86 (s, 3H), 3.83 (s,3H), 3.82 (s, 3H). MS(EI): m/z 196 M+. Retention time of 2.82 min, >99% pure. | |
With oxalyl dichloride; In dichloromethane; at 0 - 20℃; | General procedure: General procedures for preparation of benzoyl chloride(a-g): To a stirred solution of benzoic acid in dichloromethane(DCM) was added oxalyl chloride at 0 C and stirred for 3-4 hat an ambient temperature and then the reaction mixture wasevaporated under pressure to obtain the corresponding benzoylchloride which was used in the next step without furtherpurification. | |
With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: Under inert atmosphere, a mixture of carboxylic acid 21-31 ( Scheme 1 ) (1 equiv), thionyl chloride (1.5 equiv) and DMF (3-5 drops) in dichloromethane was stirred at rt until the complete consumption of the carboxylic acid (1H NMR control). The pale yellow solution was concentrated in vacuo to give the crude acid chloride 32-42 ( Scheme 1 ) as a yellow pale solid in quantitative yield | |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;Inert atmosphere; | To a stirred solution of acid 9 (320 mg, 1.76 mmol) in CH2Cl2 (10 mL) under N2 atmosphere, DMF (one drop) and oxalyl chloride (0.23 mL, 2.6 mmol) were added. The mixture was stirred for 3 h at room temperature and then the solvent was removed under vacuum. The crude product acid chloride was directly used for the next reaction without further purification. A solution of compound 1114 (554 mg, 2.64 mmol) in THF (6 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.44 mL, 3.52 mmol) and i-Pr2NH (0.49 mL, 3.52 mmol) in THF (5 mL) at 0 C under N2 atmosphere. The thus produced yellowish anion was stirred at -78 C for 45 min and then a solution of crude acid chloride in THF (10 mL) was added drop wise. The reaction was stirred at the same temperature for another 45 min and then at room temperature for 4 h. 10% HCl (10 mL) was added to quench the reaction, THF was removed in vacuum and the water layer was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 12 (500 mg, 76%) as yellowish oily compound. Rf 0.3 (1:1 ethyl acetate:hexane); 1H NMR (CDCl3, 500 MHz): delta 7.89 (d, 1H, J=9.0Hz, C6?-H), 7.03 (d, 1H, J=8.5Hz, C6?-H), 6.49 (dd, 1H, J=9.0, 2.0Hz, C5?-H), 6.44 (s, 1H, C3?-H), 6.41 (d, 1H, J=8.5Hz, C5?-H), 6.36 (d, 1H, J=2.0Hz, C3?-H), 5.95 (s, 1H, C2-H), 3.78 (s, 3H, OMe), 3.75 (s, 3H, OMe), 3.74 (s, 3H, OMe), 3.73 (s, 3H, OMe), 3.72 (s, 3H, CO2Me); 13C NMR (CDCl3, 125 MHz): delta 193.1 (C), 171.0 (C), 164.9(C), 160.7 (C), 160.3(C), 157.9 (C), 133.5 (CH), 130.3 (CH), 119.5 (C), 115.6 (C), 105.7 (CH), 104.2 (CH), 98.5 (CH), 98.0 (CH), 57.2 (CH3), 55.5 (CH3), 55.5 (CH3), 55.2 (CH3), 55.2 (CH3), 52.2 (CH); HRMS (EI+) m/z 374.1370 ([M]+ C20H22O7, requires 374.1366). | |
With thionyl chloride; at 70℃; for 1h;Reflux; | Weigh 2. 7g2, 4- dimethoxy-benzoic acid in 100ml round bottom flask and placed in an oil bath at 70 C, 7. 2g was added thionyl chloride was stirred at reflux for lh. Distilled off under reduced pressure Excess thionyl chloride was then added dropwise by dissolving 1.95g of the compound (2) in 15ml pyridine, reacted at 80 C 2h, cooled and poured into ethyl acetate was added dilute hydrochloric acid, successively washed with water and saturated brine. the combined organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, without purification, redissolved in pyridine and square. 9gK0H, reacting at 100 C 30min, cooled , and poured into dilute hydrochloric acid and ethyl acetate was added, washed successively with water and saturated brine, and the combined organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, by column chromatography [the V (petroleum ether): V (ethyl acetate ester) 51] to give compound 3 as a yellow solid 2.015g (yield 57%). Compound mp 108 · 8-109 C. The product structure was confirmed by IR, NMR and MS analysis. | |
With sulfuryl dichloride; In benzene; for 3h;Reflux; | <strong>[91-52-1]2,4-Dimethoxybenzoic acid</strong> (18.2 g, 100 mmol), benzene(190 mL), and thionyl chloride (50 mL) were combined in a 500-mL, 3-necked flask. The mixture was refluxed for 3 h. Thenthe solvent and excess thionyl chloride were removed by distillation.The residual was used in the next step without any furtherpurification. | |
With thionyl chloride; at 0 - 60℃; for 2h;Inert atmosphere; | General procedure: SOCl2 (2 mL) was added to substituted benzoic acid (0.55 mmol) under nitrogen atmosphere at 0C. The resulting mixture was warmed to 60C and stirred for 2 h. After completion of the reaction, the reaction mixture was cooled to room temperature and the excess SOCl2 was removed under reduced pressure. The resulting acid chloride was kept under vacuum for 30 min and used in the next step without further purification. | |
With thionyl chloride; for 2h;Reflux; | (2)A total of 50 mL of thionyl chloride was added in portions to Compound 3 (55 g, 0.3 mol) with stirring.There is a large amount of gas generated (the reaction system needs to be connected to an acid gas absorption device),The reaction solution was initially yellow and quickly turned purple-black; after the addition of thionyl chloride, the oil bath was heated to reflux for 2 hours, after cooling, most of the thionyl chloride was removed by ordinary distillation, and cooled to room temperature, and an appropriate amount of DCM was added. Dissolving the residue in the reaction flask and concentrating again to obtain a purple-black solid-liquid mixture, which is Compound 4,It was used directly in the next step without purification. | |
With thionyl chloride; for 2h;Reflux; | General procedure: For the synthesis of thiourea (2-6), acid chloride of substituted acidwas prepared by refluxing the substituted benzoic acid with thionylchloride (1.5 eq) for 2 hr. In another two neck round bottom flask potassiumthiocyanate (KSCN) (1 eq) was suspended in 5 mL of acetone.Acid chloride was added in it and stirred for 35 min. After addingtriazole amine (1) [29] dissolved in 5 mL of acetone (dry) into reactionmixture and refluxed for one hour. Upon completion, the reactionmixture was poured in ice cold water; obtained solid precipitates werepassed through filter paper, washed and purified by using suitablesolvent [30]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With bromine; acetic acid; at 25℃; for 2h; | (Example 1); Step 1; Synthesis of 5-bromo-2,4-dimethoxybenzoic acid; <strong>[91-52-1]2,4-Dimethoxybenzoic acid</strong> (30.0 g) was suspended in acetic acid (180 mL). A bromine (27.6 g)/acetic acid (60 mL) solution was slowly added dropwise to the suspension and, after completion of the dropwise addition, the mixture was stirred at 25C for 2 hrs, and the termination of the reaction was confirmed by HPLC. An aqueous solution of sodium sulfite (2.10 g) and water (360 mL) was added dropwise to the reaction mixture. After completion of the dropwise addition, the mixture was stirred at 25C for 1 hr. Precipitated crystals were filtered, washed 4 times with water (150 mL), and vacuum dried to give 5-bromo-2,4-dimethoxybenzoic acid as white crystals (41.2 g) (96%). |
96% | With bromine; acetic acid; at 25℃; | Example 1; Synthesis of 6-(3-chloro-2-fluorobenzyl)-1-((S)-1-hydroxymethyl-2-methylpropyl)-7-methoxy-4-oxo-1,4-dihydroquinoline)-3-carboxylic Acid; Step 1; Synthesis of 5-bromo-2,4-dimethoxybenzoic Acid ; <strong>[91-52-1]2,4-Dimethoxybenzoic acid</strong> (30.0 g) was suspended in acetic acid (180 mL). A bromine (27.6 g)/acetic acid (60 mL) solution was slowly added dropwise to the suspension and, after completion of the dropwise addition, the mixture was stirred at 25 C. for 2 hrs, and the termination of the reaction was confirmed by HPLC. An aqueous solution of sodium sulfite (2.10 g) and water (360 mL) was added dropwise to the reaction mixture. After completion of the dropwise addition, the mixture was stirred at 25 C. for 1 hr. Precipitated crystals were collected by filtration, washed 4 times with water (150 mL), and vacuum dried to give 5-bromo-2,4-dimethoxybenzoic acid as white crystals (41.2 g, 96%). |
With bromine; In chloroform; | 5-Bromo-2,4-dimethoxybenzoic Acid To a solution of 2.4-dimethoxybenzoic acid (4.0 g, 0.022 mol) in chloroform (60 ml) was added bromine (1.13 ml, 0.022 mol) in chloroform (20 ml) dropwise. After stirring overnight at room temperature the precipitate was filtered off and dried to afford the title compound as a white solid (2.87 g). |
With bromine; In chloroform; | 5-Bromo-2,4-dimethoxybenzoic Acid To a solution of 2,4-dimethoxybenzoic acid (4.0 g, 0.022 mol) in chloroform (60 ml) was added bromine (1.13 ml, 0.022 mol) in chloroform (20 ml) dropwise. After stirring overnight at room temperature the precipitate was filtered off and dried to afford the title compound as a white solid (2.87 g). | |
With bromine; In chloroform; | 5-Bromo-2,4-dimethoxybenzoic acid To a solution of 2,4-dimethoxybenzoic acid (4.0 g, 0.022 mol) in chloroform (60 ml) was added bromine (1.13 ml, 0.022 mol) in chloroform (20 ml) dropwise. After stiring overnight at room temperature the precipitate was filtered off and dried to afford the title compound as a white solid (2.87 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With trichlorophosphate 1.) RT, 0.5 h, 2.) reflux, 6 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of 4-methoxy benzoic acid (0.5 g, 3.3 mmol) in 10 mL THF at 5C, triethylamine (0.46 mL, 3.3 mmol) in 5 mL THF was added drop wise and stirred. After 30 min, the cooled ethyl chloroformate solution (0.31 mL, 3.3 mmol) in 5 mL THF was added slowly and was stirred at 5C for 30 min. In the last step, the solution of sodium azide (0.42 g, 6.6 mmol) in 5 mL water was added drop-wise and stirred at room temperature overnight. The resulting mixture was extracted with ethyl acetate (3*15 mL) and the organic phase was washed with saturated sodium bicarbonate (3*30 mL) and with water (2*25 mL) and dried over MgSO4. After the ethyl acetate was removed, 0.47 g azide (80%) was obtained. Without any purification, the obtained acyl azide was used immediately. Acyl azide (0.47 g, 2.7 mmol) and 2-aminothiophene (0.34 g, 2.7 mmol) in benzene (20 mL) was stirred at 70-80C for 24 h under nitrogen. The formed precipitate was filtered off and washed with benzene. The resulting residue was purified by crystallization from EtOH and urea 1g was obtained as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: 52 percent / AlCl3 / diethyl ether / 8 h / Ambient temperature 3: 84 percent / pyridine, tetramethylammonium hydroxide / H2O / 36 h / Heating 4: 91 percent / phenol, HI / 8 h / 160 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 78 percent / conc. H2SO4 / 3 h / Heating 2: 53 percent / NaH / benzene / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tert.-butylhydroperoxide In water at 50℃; for 12h; Sealed tube; Green chemistry; | |
Multi-step reaction with 2 steps 1: permanganate 2: KMnO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid at 70℃; for 2h; | |
With sulfuric acid for 14h; Heating / reflux; | ||
With sulfuric acid at 20℃; for 12h; |
With sulfuric acid for 14h; Reflux; | 2.1 2.1 1 ml of conc. sulfuric acid is added to a solution of 100 g of 2,4-dimethoxybenzoic acid in 500 ml of methanol, and the mixture is refluxed for 14 hours. The mixture is cooled, the solvent is removed, the residue is dissolved in 1 litre of MTB, the solution is washed three times with 200 ml of water each time and dried, and the solvent is removed, giving 105.5 g of methyl 2,4-dimethoxybenzoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methylamine; In trichlorophosphate; | EXAMPLE 41 1-Methyl-2-(2,4-dimethoxyphenyl)-1H-imidazo[4,5-c]pyridine and its dihydrochloride The title base was prepared from 4-methylamino-3-amino-pyridine (prepared from 4-chloro-3-nitropyridine and methylamine followed by reduction) and 2,4-dimethoxybenzoic acid in phosphorus oxychloride as described in Example 40, m.p. 180-181 C. An acetone solution of the base was treated with ethereal HCl to give the title hydrochloride m.p. 225-227 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methylamine; In trichlorophosphate; | EXAMPLE 40 3-Methyl-2-(2,4-dimethoxyphenyl)-1H-imidazo[4,5-c]pyridine and its hydrochloride A mixture of 2,4-dimethoxybenzoic acid and 3-methylamino-4-amino-pyridine (prepared from 3-bromo-4-nitropyridine-N-oxide and methylamine followed by reduction) in phosphorus oxychloride was refluxed for 4 hours. After cooling the solid was triturated with ether and then partitioned between chloroform and saturated sodium bicarbonate. After drying over magnesium sulphate the solvent was evaporated and the residue chromatographed on silica gel. Recrystallisation from benzene-petrol gave the title base, m.p. 162-163 C. An acetone solution of the base was treated with ethereal HCl to give the title hydrochloride, m.p. 235-237 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; | Example 2 8-(2,4-Dimethoxy-phenyl)-purine A mixture of 5.5 g of <strong>[13754-19-3]4,5-diaminopyrimidine</strong> and 10.9 g of 2,4-dimethoxy-benzoic acid was triturated in a mortar. The mixture was added to 100 ml of phosphorus oxychloride and refluxed for one hour. The phosphorus oxychloride was decomposed under stirring into water, and the solution obtained was neutralized with ammonia after filtration. The precipitated product was recrystallized from water and ethanol/cyclohexane (volume ratio of 1:3). Yield: 3.5 g (27% of theory), M.P.: 218-220 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With PPA; In methoxybenzene; | Step 6a: 2,4,4'-trimethoxybenzophenone. To a reaction flask were added 5.0 g (0.030 mole) of 2,4-dimethoxybenzoic acid, 3.25 g (0.030 mole) of anisole and 30 g of polyphosphoric acid. The reaction mixture was warmed to 60-70C with stirring for 2 hours and transferred into ice water. The resulting oil was extracted with ethyl acetate, the organic layer was separated, dried, evaporated and the resulting crude product was purified by column chromatography on silica using a 4:1 mixture of toluene and ethyl acetate as eluent. A light-yellow powder (3.5 g, 43%) was produced. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium(II) trifluoroacetate; 1-Adamantanecarboxylic acid; p-benzoquinone In 1,4-dioxane; dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; optical yield given as %de; regioselective reaction; | ||
With oxygen; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With silver carbonate; copper dichloride; palladium dichloride; In tetrahydrofuran; at 110℃; for 24h; | General procedure: A mixture of carboxylic acid (1 equiv., 0.5 mmol), CuBr2 or CuCl2 (2 equiv., 1 mmol), Ag2CO3 (1 equiv., 0.5 mmol) and PdCl2 (0.1 equiv.) was heated inTHF (3 mL) under reflux at 110 oC for 24 h. After the reaction finished, the mixture was evaporated under vacuum and purified by columnchromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 1-oxothiolane; palladium(II) trifluoroacetate; propionic acid; silver carbonate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxygen; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 10h; optical yield given as %de; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With oxygen; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 10h; optical yield given as %de; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate / N,N-dimethyl acetamide / 8 h / 120 °C / Inert atmosphere 2: silver(I) acetate; potassium carbonate / N,N-dimethyl acetamide / 4 h / 160 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate / N,N-dimethyl acetamide / 8 h / 120 °C / Inert atmosphere 2: silver(I) acetate; potassium carbonate / N,N-dimethyl acetamide / 4 h / 160 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With palladium(II) trifluoroacetate; silver carbonate In dimethyl sulfoxide at 120℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium phosphate; palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,4-dioxane; dimethyl sulfoxide at 140℃; for 22h; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60% 2: 30% | Stage #1: 2,4 dimethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: methanol With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With N-iodo-succinimide; palladium diacetate; In N,N-dimethyl-formamide; at 120℃; for 3h;Inert atmosphere; Sealed tube; | A mixture of 2,4-dimethoxybenzoic acid (36.4 mg, 0.2 mmol), NIS (135.0 mg, 0.6 mmol), palladium acetate(0.9 mg, 0.002 mmol), and a stirrer were placed in the reaction tube. After replacing the inert gas, 1 ml of solvent DMF was added, Sealed reaction tube. The reaction tube was placed in an oil bath reaction reactor at 120 C and stirred for 3 hours. After cooling to room temperature, use 2 mol / L Sodium hydroxide solution to adjust pH = 10. The reaction tube was diluted with 5 ml of water and extracted with ethyl acetate. Combined extract, And dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and then extracted with ethyl acetate: petroleum ether = 0 to 1: 30 (volume ratio) The eluate was subjected to column chromatography on the crude product to give pure 4,6-dimethoxy-1,3-diiodobenzene (38.2 mg, 49%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sulfuric acid; trifluoroacetic acid; In dichloromethane; for 2h;Reflux; | While dissolving 2,4-dimethoxybenzoic acid (10 g) and 1-adamantanol (9.2 g) in dichloromethane (120 mL) and stirring the resulting solution, trifluoroacetic acid (4 mL) and concentrated sulfuric acid (6.7 mL) were dropped thereto, and then refluxed for 2 hours. The stirred mixture solution was distilled under reduced pressure. The residue was dissolved in ethanol (100 mL) and water (100 mL) and stirred, and then pH of the solution was adjusted to 6 by using 50% potassium hydroxide solution. The solid thus formed was filtered, and ethanol (30 mL) and 1N hydrochloric acid solution (120 mL) were added thereto followed by stirring thereof for 1 hour. The solid thus formed was filtered to obtain 5-adamantane-1-yl-2,4-dimethoxybenzoic acid (17 g, yield 97%). 1H-NMR (300 MHz, DMSO-d6) 12.07 (brs, 1H), 7.57 (s, 1H), 6.63 (s, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 1.99 (s, 9H), 1.71 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h; | General procedure: To a solution of 3-cyanobenzoic acid 8a (3.0 g, 19.7 mmol) in DMF was added N,O-dimethylhydroxylamine hydrochloride (2.0 g, 20.7 mmol), Et3N (2.88 mL, d = 0.73, 20.7 mmol) and EDC·HCl (4.0 g, 20.7 mmol). After the mixture was stirred for 3 h at room temperature, the solvent was removed in vacuo and the residue was dissolved in EtOAc, washed with 10% citric acid, 10% NaHCO3 and saturated NaCl, and dried over Na2SO4. Then, the solvent was removed to give a colorless oil of compound 9a (3.0 g, 79%). |
80% | 4.2.4 1-(2,4-Dimethoxyphenyl)-2-(pyridin-2-yl)ethan-1-one (17) In an oven dried 100?mL round-bottom flask was placed 2,4-dimethoxybenzoic acid (1.0?g, 5.49?mmol) and anhydrous dichloromethane (45?mL). The solution was stirred at rt and treated with 1-methylpiperidine (3.35?mL, 27?mmol). After stirring for 10?min the solution was cooled to 0?C and pivaloyl chloride (0.79?g, 0.81?mL, 6.59?mmol) was added via syringe dropwise. The solution was stirred for 2?h. N,O-Dimethyl hydroxylamine hydrochloride (0.803?g, 8.23?mmol) was added, and the mixture was stirred at room temperature for 24?h. The yellow solution was poured into HCl (80?mL, 1?M). The organic layer was sequentially washed with saturated NaHCO3 and brine (80?mL) and dried over MgSO4. After concentration, the yellow oil was dried under vacuum to afford the amide (16) as a white solid. 16: Yield 80%; 1H NMR (400?MHz, CDCl3) delta 7.19 (d, J?=?8.4?Hz, 1H), 6.47-6.43 (m, 2H), 3.78 (s, 6H), 3.55 (bs, 3H), 3.23 (bs, 3H); 13C NMR (100?MHz, CDCl3) delta 161.8, 157.3, 129.0, 117.7, 104.3, 98.6, 60.9, 55.7, 55.4; FTIR (neat): 2964, 2935, 1642, 1606, 1513, 1311, 1289, 1118, 988, 938?cm-1. | |
80% | General procedure: In an oven dried 100 mL round-bottom flask was placed 2,4-dimethoxybenzoic acid (1.0 g, 5.49 mmol) and anhydrous dichloromethane (45 mL). The solution was stirred at rt and treated with 1-methylpiperidine (3.35 mL, 27 mmol). After stirring for 10 min the solution was cooled to 0 C and pivaloyl chloride (0.79 g, 0.81 mL, 6.59 mmol) was added via syringe dropwise. The solution was stirred for 2 h. Nu,Omicron-Dimethyl hydroxylamine hydrochloride (0.803 g, 8.23 mmol) was added, and the mixture was stirred at room temperature for 24 h. The yellow solution was poured into HC1 (80 mL, 1 M). The organic layer was sequentially washed with saturated NaHC03 and brine (80 mL) and dried over MgS04. After concentration, the yellow oil was dried under vacuum to afford the amide (16) as a white solid. Compound 16: Yield 80%; NMR (400 MHz, CDCh) delta 7.19 (d, J = 8.4 Hz, 1H), 6.47- 6.43 (m, 2H), 3.78 (s, 6H), 3.55 (bs, 3H), 3.23 (bs, 3H); 13C NMR (100 MHz, CDCh) delta 161.8, 157.3, 129.0, 117.7, 104.3, 98.6, 60.9, 55.7, 55.4; FTIR (neat): 2964, 2935, 1642, 1606, 1513, 1311, 1289, 1118, 988, 938 cm-1. |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃; for 14h; | A flame-dried round bottom flask, containing 2,4-dimethoxybenzoic acid (1.0 equiv) and N,O-dimethylhydroxylamine hydrochloride (1.2 equiv) dissolved in anhydrous dichloromethane (0.2 M), was cooled to 0 C with stirring. At 0 C, triethylamine (1.2 equiv) was added to the solution dropwise via syringe and stirred for 15 minutes. Next, at 0 C, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI*HCl, 1.2 equiv) was added to the stirring solution in one portion. The reaction was allowed warm to room temperature and stir overnight. The reaction was then quenched with 2 N HCl and diluted with DCM. The organic layer was separated and washed twice with DI water. The combined organics were then washed with brine, dried with anhydrous MgSO4, filtered, and concentrated to afford a crude oil, which was taken on to the Grignard addition without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With silver (II) carbonate; palladium diacetate; propionic acid; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium phosphate; copper quinolate; tetra-(n-butyl)ammonium iodide In water; dimethyl sulfoxide at 120℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃;Inert atmosphere; | General procedure: Triphenylphosphine(300mg, 1.14mmol), 2-methoxybenzoic acid (155mg, 1.02mmol) and di-isopropyl azodicarboxylate (226 ml, 1.14mmol) were added to a stirred solution of 2 (300mg, 0.34mmol) in dry THF (10ml) at 0 C. After stirring for 2 h at the same temperature, the reaction mixture was diluted with ice water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 15B3:1) to give 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; | A solution of 1.82 g of 2, 4-dimethoxy benzoic acid, 1.23 g of 4-anisidine and 0.1 g of DMAP in 10 mL of DMF was treated with 2.06 g of DCC at 0C. After stirring for 1 hour at 0C, the reaction mixture was allowed to warm to room temperature and stirred overnight, then filtrated, concentrated and subjected to column chromatography to afford 12a as white powder in 87% yield.43 GC/MS: m/z 287 (M+, 100%). 1H-NMR (CDC13, 300 MHz): 5 = 3.81 (s, 3H), 3.88 (s, 3H), 4.02 (s, 3H), 6.53 (d, J = 2.4 Hz, 1H), 6.65 (dd, J = 2.1 and 8.4 Hz, 1H), 6.90 (d, J = 9.0 Hz, 1H), 7.57 (d, J = 8.7 Hz, 2H), 8.26 (d, J = 8.7 Hz, 1H), 9.55 (s, 1H). 13C-NMR (CDC13, 75 MHz): delta = 55.5, 55.6, 56.2, 98.8, 105.6, 114.1, 114.8, 122.1, 131.8, 134.2, 156.1, 158.5, 163.0, 163.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; | General procedure: A mixture of 2,5-dimethoxybenzoic acid (151.0 mg, 0.83 mmol), EDCI (192.0 mg, 1.0 mmol), HOBt (135.0 mg, 1.0 mmol) and 56 (300.0 mg, 1.0 mmol) in CH2Cl2 (10.0 mL) was stirred at room temperature overnight. The organic layer was washed successively with 2 M HCl and 2 M NaOH, then dried (MgSO4), filtered, concentrated and purified by normal phase column chromatography (0-100% ethyl acetate in hexanes) to afford 336.0 mg (88%) of 57a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; In 1,4-dioxane; at 130℃; for 24h;Inert atmosphere; | General procedure: An oven-dried reaction vessel was charged with [RuCl2(pcymene)]2 (Ru*, 6.1 mg, 0.01 mmol, 5 mol%), acids (0.2mmol), isocyanates (0.5 mmol), K2HPO4 (17.4 mg, 0.1 mmol), and KH2PO4 (13.6 mg, 0.1 mmol). After the vessel was evacuated and purged with argon three times, 1,4-dioxane (0.5 mL) was added to the system by syringe. The mixture was stirred at 130 C for 24 h. When the reaction was complete, the resulting mixture was cooled to room temperature and filtered through a short silica-gel pad. The mixture was then concentrated in vacuo to give a residue, which was purified by preparative thin layer chromatography (TLC) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With N-iodo-succinimide; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere; Sealed tube; | A mixture of 2,4-dimethoxybenzoic acid (36.4 mg, 0.2 mmol), NIS (47.3 mg, 0.21 mmol), palladium acetate(0.9 mg, 0.002 mmol), and a stirrer were placed in the reaction tube. After replacing the inert gas, 1 ml of solvent DMF was added, Sealed reaction tube. The reaction tube was placed in an oil bath reaction reactor at 80 C and stirred for 3 hours. After cooling to room temperature, use 2 mol / L of hydrogen Sodium oxide solution to adjust pH = 10. The reaction tube was diluted with 5 ml of water and extracted with ethyl acetate. Merge the extract and Dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and washed with ethyl acetate: petroleum ether = 0 to 1: 30 (volume ratio) The crude product was subjected to column chromatography to give pure 2,4-dimethoxyiodobenzene (23.8 mg, 45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | n-BuLi (2.5 M in THF, 3.3 mL, 8.3 mmol) was added drop wise to a stirred solution of 1-bromo-2,4-dimethoxybenzene (7) (1.5 g, 6.9 mmol) in THF (15 mL) at -78 C under N2 atmosphere. After 30 min, CO2 gas was passed through the solution during 45 min of time and the mixture was allowed to warm up to room temperature. THF was removed in vacuum and the mixture was treated with saturated NaHCO3 solution (40 mL). The water layer was washed with ethyl acetate (2*20 mL) and then acidified with conc. HCl. The mixture was extracted with ethyl acetate (2*75 mL). The organic layer was washed with water (2*30 mL), brine (30 mL), dried (Na2SO4), filtered and concentrated. Recrystallization from ethyl acetate produced 9 (1.15 g, 91%) as white solid. Rf 0.3 (1:1 ethyl acetate:hexane); mp 103-105 C (lit.22 107-109 C); 1H NMR (CDCl3, 500MHz): delta 8.10 (d, 1H, J=9.0Hz, C6-H), 6.61 (dd, 1H, J=9.0, 2.0Hz, C5-H), 6.50 (d, 1H, J=2.0Hz, C3-H), 4.01 (s, 3H, OMe), 3.86 (s, 3H, OMe); 13C NMR (CDCl3, 125MHz): delta 179.9 (C), 165.2 (C), 160.2 (C), 135.2 (CH), 110.1 (C), 106.2 (CH), 98.5 (CH), 56.4 (CH3), 55.7 (CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With dmap; triethylamine; In acetonitrile; at 20℃; | General procedure: 2-Methoxybenzoic acid (1a, 761 mg, 5.0 mmol), triethylamine (725 muL, 5.2 mmol), and 4-DMAP (61 mg, 0.5 mmol) was added to a solution of N-methoxy-N-methyl carbamoyl chloride (619 mg, 5.0 mmol) in acetonitrile at room temperature and stirred for 1.5 h. After evaporation of acetonitrile, the mixture was poured into saturated NaHCO3 solution (40 mL) and extracted with methylene chloride (3 × 25 mL). The condensed residue was purified with short pathway silica gel column chromatography using 50% EtOAc/n-hexane to give 2a (820 mg, 84%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.3% | 1.646g of 2,4-dimethoxybenzoic acid in the dropwise addition of thionyl chloride 4.271g,The reflux reaction 1h,The excess of thionyl chloride was distilled off under reduced pressure,Then it was added to dissolve 1. 00 g2-hydroxy-6-methoxyacetophenone (2) in 8 mL of anhydrous pyridine,The reaction at 100 C 2h,Add ethyl acetate cooling into the water extraction,Then washed with dilute hydrochloric acid and water in that order, Dried over anhydrous sodium sulfate, the solvent removed,Column chromatography [V (petroleum ether): V (ethyl acetate) = 4: 1] afforded 1.69 g of an oil, 86.3% yield. | |
With pyridine; thionyl chloride; at 100℃; for 2h; | Weigh 1.316g of 2,4-dimethoxybenzoic acid, add 3.440g of thionyl sulfoxide, reflux for 1h, evaporate under vacuum to remove excess of thionyl chloride, then add it to dissolve 0.800g of the first The intermediate product is in 8 mL of anhydrous pyridine and reacted at 100 C. for 2 h. Ethyl acetate is added, and the mixture is cooled and poured into water. The organic phase is washed with dilute hydrochloric acid and water in that order.After drying over sodium sulfate, the solvent was removed under reduced pressure to obtain an intermediate compound. The intermediate compound was dissolved in pyridine without purification, 0.540 g of pre-heated potassium hydroxide powder was added, stirred for 30 minutes, cooled to room temperature, and acetic acid was added. The ethyl ester was cooled and poured into water. The organic phase was washed with dilute hydrochloric acid and water, dried over anhydrous sodium sulfate, and then subjected to column chromatography V (petroleum ether): V (ethyl acetate) = 4:1 to give a yellow oil. The second intermediate product (0.976 g, yield 49.01%) was confirmed by IR, NMR and MS analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With dipotassium hydrogen phosphate; palladium diacetate at 140℃; for 36h; Inert atmosphere; Sealed tube; | 3 General procedure 1: synthesis of the isobenzofuran-1(3H)-ones (7-10) General procedure: Under a N2 atmosphere, a sealed tube was charged with theappropriate benzoic acid (1 mmol), palladium acetate (22.4 mg,0.1 mmol), dipotassium phosphate (K2HPO4, 522.5 mg, 3 mmol)and dibromomethane (4 mL). The contents of the tube weredegassed by flushing N2 through a needle for 10 min. The tube wasthen sealed, and heated in an oil bath at 140 C for 36 h. The tubewas then allowed to cool to room temperature, the content wasdiluted with CH2Cl2 (20 mL), and filtered through celite. The filtratewas washed with 1 M HCl (20 mL) and brine (2 15 mL), and wasdried (MgSO4). The solventwas evaporated under reduced pressureand the residue was either subjected to flash column chromatography(10% methanol in chloroform) or recrystallised from chloroform/hexane mixture (1:3).2.5.2.3 5,7-Dimethoxyisobenzofuran-1(3H)-one 41 (9) Following the general procedure 1 using 2,4-dimethoxybenzoic acid 6 (182 mg). The benzofuran 9 was isolated after column chromatography as a white solid (112.5 mg, 58%). Spectral data of the isolated benzofuran 9 are in agreement with that reported. 41 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With tert.-butylhydroperoxide; iron(III) chloride; In pyridine; water; toluene; at 85℃; for 8h;Inert atmosphere; Sealed tube; | In the reaction flask equipped with a magnetic 20mL was added <strong>[91-52-1]2,4-dimethoxy-benzoic acid</strong> (0.055g, 0.3mmol),FeCl3 (0.0049 g, 0.03 mmol),TBHP (0.116 g, 0.9 mmol,70% aqueous solution),DMF (1 mL),Toluene (1 mL),Pyridine (0.118 g, 1.5 mmol),Fill it with argon,Tighten the cap,External temperature 85 C closed reaction 8h;Gas chromatography monitoring;After the reaction is completed,Rotary evaporation to remove the solvent,After column chromatography (ethyl acetate: petroleum ether = 4:1), a white solid was obtained.Yield 96%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triethylamine; at 150℃; for 16h; | General procedure: Benzoic acid (244 mg, 2.0 mmol) and Et3N (243 mg, 2.4 mmol) were reacted in DMSO (8.0 mL) at 150 oC for 16 h. The mixture charged to separating funnel added water, extracted with EtOAc. The organic layer washed with water many times for removing water, dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography on silica gel.(eluent : Hexane / ethyl acetate = 10 / 1). |
79% | With triethylamine; at 160℃; under 760.051 Torr; for 20h;Schlenk technique; Inert atmosphere; Green chemistry; | General procedure: An oven-dried Schlenk tube equipped with a stir bar was charged with carboxylic acid (0.2 mmol) and Et3N (28 mL, 0.2 mmol, 1 equiv). The tube was fitted with a rubber septum, and then it was evacuated and refilled with nitrogen three times. Under nitrogen, DMSO (2 mL) was added via syringe. The rubber septum was replaced with a Teflon screwcap under nitrogen flow, and the Schlenk tube was pressurized to 1 atm. With stirring, the reaction mixtures were heated at 160 C for the indicated amount of time (unless otherwise specified). After cooling to room temperature, the reaction mixture swere diluted with ether (10 mL) and filtered through a pad of silica gel that was then washed with ether (10 mL X 3). The combined organic phase was washed with brine (20 mL 2), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography over silica gel to provide the corresponding product with ethyl acetate/hexane as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Sealed tube; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In tetrahydrofuran for 24h; Inert atmosphere; Sealed tube; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: thionyl chloride / 2 h / Reflux 2: aluminum (III) chloride / dichloromethane / 4.5 h / 20 °C / Molecular sieve; Inert atmosphere; Cooling with ice 3: Pyridine hydrobromide; sodium chloride / 1 h / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 10 h / 82 °C 5: sodium hydroxide; water / ethanol / 3 h / 20 - 70 °C 6: thionyl chloride / 3.33 h / Cooling with ice 7: potassium carbonate / acetone / 5.5 h / 68 °C / Inert atmosphere 8: sodium hydroxide; water / ethanol / 60 °C 9: acetic acid / water / 46 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; In dimethyl sulfoxide; at 140℃; under 760.051 Torr; for 20h;Schlenk technique; Green chemistry; | General procedure: An oven-dried Schlenk tube equipped with a stir bar was charged with aryl carboxylic acid (0.2 mmol), Ag2SO4 (6.2 mg, 0.02 mmol, 0.1 equiv.), Cu(OAc)2 (36.3 mg, 0.2 mmol, 1 equiv.), K4Fe(CN)6 (13.2 mg, 0.036 mmol, 0.18 equiv.) and 2,9-dimethyl-1,10-phenanthrolinium (12.5 mg, 0.06 mmol, 0.3 equiv.). The tube was fitted with a rubber septum, and then it was evacuated and refilled with dioxygen three times. Under dioxygen, DMSO (4 mL) was added via syringe. The rubber septum was replaced with a Teflon screwcap under dioxygen flow, and the Schlenk tube was pressurized to 1 atm. With stirring, the reaction mixtures were heated at 140 C for the indicated amount of time (unless otherwise specified). After cooling to room temperature, the reaction mixtures were diluted with ether (10 mL) and filtered through a pad of silica gel that was then washed with ether (10 mL *3). The combined organic phase was washed with brine (20 mL *2), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified using flash column chromatography over silica gel to provide the corresponding product with ethyl acetate/hexane as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 5h; | General procedure: An oven-dried Schlenk tube equipped with a stir bar was charged with carboxylic acid (0.2 mmol) and K2CO3 (55.3 mg, 0.4 mmol, 2 equiv.). The tube was fitted with a rubber septum, DMSO (1 mL) and CH2Cl2 (1 mL) was added via syringe at air. With stirring, the reaction mixtures were heated at 130 C for 5 h (unless otherwise specified), and then cooled down to room temperature. The resultant mixture was filtered through a short plug of silica gel and then concentrated in vacuo. The residue was then purified by flash chromatography on silica gel to provide the corresponding product. For the substrates 26, 31 were heated at 140 C for 8 h under otherwise identical conditions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With palladium diacetate; caesium carbonate; sodium sulfate; In N,N-dimethyl-formamide; at 150℃; for 12h;Inert atmosphere; | 513 mg (3 mmol) p-methylbromobenzene 1a, 546 mg (3 mmol) 2,4-dimethoxybenzoic acid 3i and 511 mg (3.6 mmol) were added to a 25 mL round bottom flask at room temperature. Sodium sulfate 2, then 10 mL DMF,135 mg (0.6 mmol) of palladium acetate and 1956 mg (6 mmol) of cesium carbonate, stirred at 150 C for 12 hours, reacted in nitrogenUnder gas protection. After cooling, 10 mL of saturated NaCl aqueous solution was added to the system, and extracted with ethyl acetate three times for 10 times each time.The organic phase is combined with anhydrous Na2SO4, and the solvent is distilled off. The silica gel column of 200-300 mesh is used to obtain p-tolyl 2,4-Dimethoxyphenyl sulfone 4j pure 797 mg, yield 91%, colorless oily liquid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With trifluoroacetic acid; trifluoroacetic anhydride at 20℃; for 12h; | 4.1.2. General procedure for the synthesis of 4a-4u General procedure: Trifluoroacetic acid anhydride (TFAA, 2 mmol) was added to a solution of 1-methoxynaphthalene 2 (1.5 mmol) and various commercial available aromatic carboxylic acid (1 mmol) in Trifluoroacetic acid (TFA, 1 mL) and stirred at room temperature for 12 h. After the completion of the reaction, the solvent was removed under reduced pressure and the residue was purified by chromatography to give the desired products 4a-4u. Spectral data of all title compounds (4a-4u) were provided in Supplementary Material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.1% | With oxygen; nitric acid at 80℃; for 0.166667h; | 6-7 General procedure: Open the bottom valve of the p-nitrotoluene storage tank and the bottom valve of the nitric acid storage tank, put the raw material p-nitrotoluene and 30% nitric acid into the upper tank 3 and mix them uniformly. The ratio of nitric acid to p-nitrotoluene is 5 :1. Turn on the feed pump, control the flow rate to 200Kg/h, make the residence time of the reaction liquid in the loop reactor be 300s, turn on the loop reactor 6, make the small diameter sleeve 62 rotate at 1000 rpm, turn on the oxygen Inlet gas, the purity of oxygen is 99.0%; the temperature control system is turned on, and the heat transfer oil enters the heat exchange jacket 64 of the small diameter sleeve 62 and the large diameter sleeve 61 to heat the reaction liquid. After reaching the reaction temperature of 190°C, the temperature control system will keep the reaction temperature of the system at 190±5°C to make the system react steadily. After the system produces qualified products, put the reaction liquid into the crystallization kettle (5) 1. After the filling factor of the crystallization kettle (5) reaches 70%, switch to the crystallization kettle (5) two and the crystallization kettle (5) one side The temperature is lowered while stirring, and after the temperature is lowered to 80-85°C, it is placed in an automatic centrifuge for centrifugation, cleaning, drying, and then sent to packaging. The purity of the liquid phase is 99.9%, and the molar yield is 99.1%. |
Tags: 91-52-1 synthesis path| 91-52-1 SDS| 91-52-1 COA| 91-52-1 purity| 91-52-1 application| 91-52-1 NMR| 91-52-1 COA| 91-52-1 structure
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