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CAS No. : | 14804-39-8 | MDL No. : | MFCD00024537 |
Formula : | C9H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HSDNHFOJTRMGER-UHFFFAOYSA-N |
M.W : | 181.19 g/mol | Pubchem ID : | 139835 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.69 |
TPSA : | 55.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.67 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 2.45 |
Log Po/w (WLOGP) : | 2.22 |
Log Po/w (MLOGP) : | 2.07 |
Log Po/w (SILICOS-IT) : | 0.59 |
Consensus Log Po/w : | 1.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.72 |
Solubility : | 0.348 mg/ml ; 0.00192 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.25 |
Solubility : | 0.102 mg/ml ; 0.000563 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.68 |
Solubility : | 0.379 mg/ml ; 0.00209 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.63 |
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: |
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* 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 |
---|---|---|
68% | With sulfuric acid; nitric acid; acetic acid at 0 - 20℃; for 3h; | |
68% | With sulfuric acid; nitric acid; acetic acid at 0 - 20℃; for 3h; | |
65% | With nitric acid; acetic acid at 0 - 65℃; |
62% | With nitric acid | 3 Synthesis of 2,6-Dimethyl-4-nitroanisole (3) EXAMPLE 3 Synthesis of 2,6-Dimethyl-4-nitroanisole (3) 2,6-Dimethylanisole (2, 36 g, 260 mmol) was added dropwise over 0.5 h to stirred cold cone. nitric acid (200 mL) contained in round-bottom flask; stirring at room temperature was continued for 18 h. The mixture was poured onto crushed ice contained in a 1-L beaker. The resulting bright yellow solid was vacuum-filtered and dried. Recrystallization from ethanol-water gave 2,6-dimethyl-4-nitroanisole (3, 29 g, 62% yield) as a pale yellow solid, mp 90°-91° C. (lit.: Burton, G. W.; Joyce, A.; Ingold, K. U. Arch. Biochem. Biophys., 1982, 221, 281; 89°-91° C.). |
61% | With nitric acid; acetic acid In water at 0 - 65℃; | 2,6-dimethyl-4-nitroanisole (16a) To an ice-cold, stirred solution of 2,6-dimethylanisole 15 (40.00 g,294 mmol) in glacial acetic acid (60 mL) was added dropwise 70% nitric acid (60 mL). After the addition was complete and gas evolution began to subside, the solution was slowly heated to 65 oC resulting in the formation of a pale yellow solution. [CAUTION: It is essential to keep the reaction temperature below 70 oC at all times as, above this, the mixture on occasions detonated with extreme violence; protection by a blast screen in recommended in any event]. The solution was then allowed to cool to ambient temperature and diluted with water (300 mL). Nitrogen was bubbled through the resulting deep brown solution for ca. 0.5 h to remove most of the nitrogen oxides present. The resulting yellow precipitate was separated by vacuum filtration and washed with copious water then crystallised from ethanol to give the nitroanisole 16a (32.6 g, 61%), mp 91.5-93.5 oC (lit.18 mp89-91 oC); 1H NMR δ 2.28 (s, 6H, 2 x Me), 3.71 (s, 3H, OMe), 7.83 (s, 2H, ArH); 13C NMR δ 16.8 (2x Me), 60.3 (OMe), 124.6 (2 x ArCH), 132.7 (2 x ArC), 143.8 (ArC), 162.8 (ArC); m/z (APCI) 152(M-29, 100%). |
With nitric acid; acetic anhydride | ||
With tetrachloromethane; Nitrogen dioxide | ||
With nitric acid; acetic acid at 60 - 70℃; | ||
(nitration); | ||
With nitric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogenchloride; acetic acid; zinc In water; ethyl acetate at 0 - 20℃; for 4h; | |
98% | In ethanol | 4 Synthesis of 4-Amino-2,6-dimethylanisole (4) EXAMPLE 4 Synthesis of 4-Amino-2,6-dimethylanisole (4) 2,6-Dimethyl-4-nitroanisole (3, 29 g, 160 mmol), 10% Pd-C (200 mg) and ethanol (300 mL) were placed in a 500-mL Parr hydrogenation flask and hydrogenated at 50 psi for 24 h. The resulting solution was filtered through a silica gel column using ethyl acetate as eluent. Concentration of the solvent and drying under vacuum gave 23.7 g (98% yield) of 4-amino-2,6-dimethylanisole (4) as a brown-colored solid, mp 59°-60° C. (lit.: Bruice, T. C.; Kharasch, N.; Winzler, R. J. J. Org. Chem. 1953, 18, 83; 63° C.). |
97% | With hydrogenchloride; acetic acid; zinc In ethyl acetate at 0 - 20℃; for 4h; |
96% | With iron(III) chloride; pyrographite; hydrazine hydrate In methanol Heating; | |
91% | With palladium 10% on activated carbon; cyclohexene In ethanol at 80℃; | |
91% | With palladium 10% on activated carbon In ethanol; cyclohexane at 80℃; for 14h; | 4-amino-2,6-dimethylanisole (16b) To a suspension of 10% Pd-C (0.65 g) in ethanol (130 mL) at rt was added portion wise the foregoing nitroanisole 16a (10.00 g, 55 mmol) followed by cyclohexene (32 mL, 330 mmol). The mixture was then heated under reflux for 14 h, cooled to rt and filtered through celite. The filter cake was washed with ethanol and the combined filtrates evaporated to leave the sensitive aniline 16b (7.56 g, 91%) as a brown solid which was sufficiently pure for further use and which showed mp 62-63 oC (lit.33 mp 60-61 oC), IR (KBr) 3772, 3612, 3397, 1605, 1487, 1340,1219, 1150, 1016 cm-1; 1H NMR δ 2.24 (s, 6H, 2 x Me), 3.47-3.51 (br s, 2H, NH2), 3.69 (s, 3H, OMe),6.39 (2, 2H, 2 x ArH); 13C NMR δ 16.5 (2 x Me), 60.4 (OMe), 115.7 (2 x ArCH), 131.9 (2 x ArC),142.5 (ArC), 150.0 (ArC); m/z (APCI) 152 (M + 1, 100%). |
67% | With hydrogenchloride; tin; acetic acid for 18h; | 3,5-Dimethyl-4-methoxyaniline. 2,6-Dimethyl-4-nitroanisole(1.18 g, 6.53 mmol) and tin powder (2.52 g, 21.2 mmol) were stirred in an HCl/AcOH mixture (1.3/13.0 mL).After 18 h, the reaction was diluted with H2O (100 mL) and neutralized with NaHCO3, then extracted into EtOAc (100 mL).The organics were washed with H2O (2x25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to afford 3,5-dimethyl-4-methoxyaniline as a pale orange solid (657 mg, 67%).1H-NMR (500 MHz, CDCl3)d6.34-6.36 (m, 2H), 3.65 (s, 3H), 3.40 (br s, 2H), 2.20-2.21 (m, 6H);13C-NMR (125 MHz, CDCl3)d149.62, 142.08, 131.45, 115.29, 59.97, 16.07; ESI-MS 152m/z[MH]+, C9H14NO requires 152. |
With diethyl ether; nickel Hydrogenation; | ||
With ethanol; platinum Hydrogenation; | ||
With hydrogenchloride; iron | ||
With hydrazine hydrate | ||
With hydrogen In ethanol | 60.3 6'-Methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline] Step 3: 4-Methoxy-3,5-dimethylaniline To a solution of 2-methoxy-1,3-dimethyl-5-nitrobenzene (12 g) in ethanol in a Parr hydrogenation bottle, was added Pd/C (0.24 g, 10%). The mixture was shaken at 50 psi of H2 in the hydrogenator overnight. The reaction mixture was filtered through Celite and the solvent was removed by evaporation. The crude residue was purified by column chromatography (10% ethyl acetate/hexane), giving 4-methoxy-3,5-dimethylaniline as a light yellow solid (8.2 g). 1H-NMR (300 MHz, CDCl3) δ=6.18 (s, 1H), 3.711 (s, 3H), 2.29 (s, 6H) ppm. MS: m/z 152 (100, M+H)+ | |
With palladium on activated charcoal; hydrogen In ethanol at 20℃; | ||
With 5%-palladium/activated carbon; hydrogen In methanol; water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 72h; | 2,6-Dimethyl-4-nitrophenol(1.18 g, 7.06 mmol), iodomethane (0.53 mL, 8.51 mmol), and K2CO3(1.18 g, 8.54 mmol) were stirred in DMF (7.0 mL) at room temperature.After 3 days, the reaction was diluted with H2O and the precipitate was filtered, rinsed with H2O, and dried to afford2,6-dimethyl-4-nitroanisoleas a pale yellow powder (1.23 g, 96%).1H-NMR (500 MHz, CDCl3)d7.92 (s, 2H), 3.79 (s, 3H), 2.36 (s, 6H);13C-NMR (125 MHz, CDCl3)d162.41, 143.49, 132.32, 124.25, 59.88, 16.38; ESI-MS 182m/z[MH]+, C9H12NO3requires 182; RP-HPLC: >99% pure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With nitric acid; acetic acid In dichloromethane for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 73 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 84 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 76 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 74 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 64 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 78 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 72 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 70 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 69 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 70 percent / molecular sieves 4 Angstroem / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 73 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 73 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 84 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 84 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 4 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 4 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 4 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 75 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 4 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 76 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 76 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 74 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 74 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 64 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 64 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 78 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 78 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 2 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 72 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 4 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 72 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 4 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 70 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 69 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 69 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / FeCl3*6H2O; NH2NH2*H2O; charcoal / methanol / Heating 2: 70 percent / molecular sieves 4 Angstroem / toluene / Heating 3: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetone; for 3.0h;Heating / reflux; | Step 2: 2-Methoxy-1,3-dimethyl-5-nitrobenzene <strong>[16947-63-0]2,6-Dimethyl-4-nitroanilin</strong>e (15 g) Me2SO4 (22 g) and K2CO3 (23 g) were dissolved in 150 mL acetone and refluxed for 3 hours. The reaction mixture was filtered and concentrated. The organic residue was dissolved in warm hexane and let to crystallize out in the fridge. After filtration, 2-methoxy-1,3-dimethyl-5-nitrobenzene was collected as white solid (12 g). 1H-NMR (300 MHz, CDCl3): delta=7.95 (s, 2H), 3.80 (s, 3H), 2.38 (s, 6H) ppm. MS: m/z 182 (100, M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43.4 g (87%) | With hydrogenchloride In N,N-dimethyl-formamide | A.1.b Example A.1 b) A mixture of (3,4-dichlorophenyl)acetonitrile (0.149 mol) in DMF (100 ml) was stirred at 0° C. under N2 flow. Sodium hydride (0.223 mol) was added portionwise. The mixture was stirred at 0° C. under N2 flow for 1 hour. A mixture of, 2-methoxy-1,3-dimethyl-5-nitrobenzene (0.149 mol) in DMF (100 ml) was added dropwise at 0° C. under N2 flow. The mixture was stirred at RT for 6 hours, then cooled, hydrolized with H2O and with HCl 3N and extracted with EtOAc. The organic layer was separated, washed several times with H2O, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 43.4 g (87%) of (+-)-α-(3,4-dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile (interm. 48). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: acetic acid; hydrogenchloride; zinc / water; ethyl acetate / 4 h / 0 - 20 °C 2.1: bromine / dichloromethane / 0.75 h / 20 °C 3.1: sulfuric acid / ethanol / 0.08 h 3.2: 1.25 h / 20 - 90 °C 4.1: boron tribromide / dichloromethane / 2 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C 6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / 85 °C 7.1: sodium hydride / acetonitrile; Petroleum ether / 0.17 h / 0 °C 7.2: 16 h / 0 - 20 °C 8.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 20 h / 20 °C 9.1: trimethylsilyl bromide / dichloromethane / 0.75 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid; hydrogenchloride; zinc / water; ethyl acetate / 4 h / 0 - 20 °C 2: bromine / dichloromethane / 0.75 h / 20 °C | ||
Multi-step reaction with 2 steps 1: acetic acid; zinc; hydrogenchloride / ethyl acetate / 4 h / 0 - 20 °C 2: bromine / dichloromethane / 0.75 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; hydrogenchloride; zinc / water; ethyl acetate / 4 h / 0 - 20 °C 2.1: bromine / dichloromethane / 0.75 h / 20 °C 3.1: sulfuric acid / ethanol / 0.08 h 3.2: 1.25 h / 20 - 90 °C | ||
Multi-step reaction with 3 steps 1.1: acetic acid; zinc; hydrogenchloride / ethyl acetate / 4 h / 0 - 20 °C 2.1: bromine / dichloromethane / 0.75 h / 20 °C 3.1: sulfuric acid / ethanol / 0.08 h / 20 °C 3.2: 1.25 h / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 2-iodo-1-methoxy-4-nitrobenzene With tetrabutylammomium bromide; potassium carbonate; palladium dichloride In N,N-dimethyl acetamide Schlenk technique; Inert atmosphere; Stage #2: carbonic acid dimethyl ester In N,N-dimethyl acetamide at 105℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With calcium hydroxide In N,N-dimethyl-formamide at 80℃; for 36h; Sealed tube; | General Methylation Procedure A (DMF Conditions) General procedure: A 10-mL glass reaction tube fitted with a resealable Teflon valve wasequipped with a magnetic stir bar and charged with the heteroatomnucleophile substrate (1.0 mmol, 1.0 equiv), Ca(OH)2 (100 mg, 1.35mmol, 1.35 equiv), TMP (0.20 mL, 1.7 mmol, 1.7 equiv), and DMF (1.0mL). The flask was sealed and stirred at 80 °C (or at RT for some thiolsubstrates) until TLC indicated complete conversion. The reaction wasthen worked up as described below. Workup Procedure A After complete conversion, 1 N HCl (5 mL) was added and the mixturewas extracted with CH2Cl2 (10 mL). The organic phase was separated,washed with H2O (20 mL), dried over Na2SO4, filtered, and then concentratedin vacuo. The resulting residue was purified by silica gelcolumn chromatography to afford the desired methylated product.Workup Procedure B After complete conversion, petroleum ether (5 mL) was added, andthe solid was smashed into fine particles using a spatula and sonicatedfor 5 min. The resulting residue was then directly subjected to silicagel column chromatography to afford the desired methylated product.Workup Procedure C After complete conversion, CH2Cl2 (5 mL) was added, and the mixturewas filtered through a pad of Celite, washed with H2O (10 mL), andextracted with EtOAc (5 × 20 mL). The organic phase was separated,dried over Na2SO4, filtered, and concentrated in vacuo. The resultingresidue was purified by silica gel column chromatography to affordthe desired methylated product. |
Tags: 14804-39-8 synthesis path| 14804-39-8 SDS| 14804-39-8 COA| 14804-39-8 purity| 14804-39-8 application| 14804-39-8 NMR| 14804-39-8 COA| 14804-39-8 structure
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