Structure of 3,4-Dimethoxyaniline
CAS No.: 6315-89-5
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CAS No. : | 6315-89-5 |
Formula : | C8H11NO2 |
M.W : | 153.18 |
SMILES Code : | NC1=CC=C(OC)C(OC)=C1 |
MDL No. : | MFCD00008394 |
InChI Key : | LGDHZCLREKIGKJ-UHFFFAOYSA-N |
Pubchem ID : | 22770 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.48 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.68 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.87 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.2 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.74 |
Solubility | 2.78 mg/ml ; 0.0181 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.61 |
Solubility | 3.79 mg/ml ; 0.0248 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.28 |
Solubility | 0.809 mg/ml ; 0.00528 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.47 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.34 |
* 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 |
---|---|---|
90% | In ethanol; at 100℃; for 4h; | 4-Chloro-6,7-dimethoxyquinazoline (224 mg, 1 mmol)3,4-dimethoxyaniline (183 mg, 1.2 mmol) was dissolved in ethanol (6 mL)100 C for 4 hours,After the end of the reaction, the mixture was cooled to room temperature for solid precipitation,The crude product was filtered off.Methanol recrystallization,A light yellow product (308 mg, 90%) was obtained. |
76% | In isopropyl alcohol;Reflux; | General procedure: 4-Chloroquinazolines (1 mmol) were dissolved in refluxing2-propanol (20 ml) and the substituted aniline (1 mmol) wasadded drop wise. The reaction mixture was refluxed for 3-4 h, until the reaction was complete as indicated by TLC. The precipitateformed was filtered off and washed with 2-propanol (10 ml) andthen with ether (10 ml). If no precipitate was formed, the solventwas removed under reduced pressure to yield solid product. Theproduct was recrystallized from 75% ethanol. |
71% | In isopropyl alcohol; at 90℃; | General procedure: A mixture of <strong>[13790-39-1]4-chloro-6,7-dimethoxyquinazoline</strong> (1 mmol), aniline (1 mmol) and 2-propanol (5 ml) was refluxed at 90C with stirring on oil bath for 2-3 h. Upon completion of the reaction as indicated by a single spot in TLC (Chloroform/Methanol 9:1 asmobile phase), the reaction mixture is cooled to ambient temperature and the solid product precipitated out is filtered. The filtered product is washed with cold 2-propanol and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In acetic acid; at 25℃; for 12h; | General procedure: An appropriate aniline derivative (1 and 2) (0.04 mol) and KSCN (0.16 mol, 15.5 g) weredissolved in glacial acetic acid (70 mL). A solution of bromine (0.04 mol, 2.05 mL) in glacialacetic acid (10 mL) was added dropwise. The mixture was stirred for 12 h. The solution wasfiltered and neutralized by ammonia (33%). The precipitate was filtered off, dried andrecrystallized from ethanol.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | Example 107 N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,4-dimethoxyaniline 3,4-Dimethoxyaniline (0.246 g, 1.604 mmol), triethylamine (0.162 g, 1.604 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.271 g, 1.604 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexane: ethyl acetate = 1:2) to obtain the titled compound (0.110 g, 0.216 mmol, 40percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: To a solution of the acid derivative (1mmol) in CH2Cl2 were added triethylamine (2mmol) and ethyl chloroformate (1mmol), followed by stirring at 0C for 30min. After addition of the appropriate amine derivative (1.2mmol), the mixture was stirred for an additional 1h at 0C. Then, the reaction mixture was warmed to room temperature and stirred overnight. After the solvent was evaporated under reduced pressure, acetone was added, filtered, and evaporated. The residue was dissolved in CH2Cl2, and the organic phase was washed with a 1% NaHCO3 solution and brine, dried over Na2SO4, and evaporated under vacuum. The final residue was purified by flash column chromatography (Combiflash Rf) using CH2Cl2-MeOH (0-5%) as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.78% | A mechanically stirred mixture of 3,4-dimethoxyaniline (5.36 g, 35 mmol) and 36 % HCl (50 mL) was cooled to -5 C. A solution of NaNO2 (2.90 g, 42 mmol) in 20 mL H2O was cooled to 0 C and slowly added while maintaining the temperature at -5 C. The final solution was stirred at 0 C for 30 min. A solution of KI (11.62 g, 70 mmol) in 30 mL H2O was added dropwise keeping the temperature between 0 and 5 C. The resulting mixture was stirred overnight and extracted twice with diethyl ether. The organic layer was consecutively washed with a concentrated NaHSO3 solution, 5 % NaOH and water and dried over MgSO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and dichloromethane-hexane (3:1; v/v) as the eluent to give 1, a pale yellow oil phase (6.91 g, 74.78%). 1H NMR (500 MHz, d6-DMSO, ppm): δ 7.23 (d, J = 8.38 Hz, 1H), 7.19 (s, 1H), 6.78 (d, J = 8.39 Hz, 1H), 3.75 (s, -OCH3, 3H), 3.73 (s, -OCH3, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With 2,2'-azobis(isobutyronitrile); oxygen; In acetonitrile; at 80℃; for 24h;Sealed tube; | General procedure: A sealed tube was equipped with a magnetic stir bar was charged with 1,3-di-ketone 1a (0.075 g, 0.75 mmol), aniline 2a (0.0232 g, 0.25 mmol), AIBN (0.0164 g, 0.0001 mmol), and acetonitrile (1.0 mL). The above reaction mixture was stirred at 80C under O2 atmosphere for 24 h. After completion of the reaction, the reaction was then cooled to room temperature, mixture was diluted with ethyl acetate. After removal of the solvent under reduced pressure the left out residue was purified by column chromatography using silica gel with hexane and ethyl acetate as eluent to get 3a in 82% yield (0.0278 g). The spectral data was well matched with reported values. The above procedure is followed for the synthesis of all products reported in this manuscript. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; | A solution of <strong>[848398-41-4]2,4-dichloro-5,7-dihydrofuro[3,4-d]pyrimidine</strong> (4, 1.89g, 10mmol) in DMSO (10mL) was added commercially available 3,4-dimethoxyaniline (1.53g, 10mmol) and DIPEA (2.58g, 20mmol). The solution was heated to 60C and stirred overnight. Then the solution was poured into water and extracted with EtOAc, the organic layer was washed by brine, dried with anhydrous Na2SO4, and filtered and concentrated under reduced pressure. The crude product was further purified by flash chromatography on silica gel (EtOAc/hexane=1:1) to afford 8 compound 5 (2.00g, yield 65%) as an off-white solid. 1H NMR (400MHz, CDCl3) delta: 6.90-6.81 (m, 3H), 4.88 (s, 2H), 4.42 (s, 2H), 3.92 (s, 3H), 3.89 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 90℃; for 0.0666667h;Microwave irradiation; | General procedure: Equimolar quantities of <strong>[3012-80-4]1-methyl-1H-benzo[d]imidazole-2-carbaldehyde</strong> and the respective aniline derivative were placed in microwave vial, and the reaction mixture was irradiated at 90 C during 4 min. After cooling to room temperature, the resulting residue was then purified by recrystallization in ethanol to give the pure Schiff base. N-(4-methoxyphenyl)-1-(1-methyl-1H-benzo[d]imidazol-2-yl)methanimine (L1). |
Tags: 6315-89-5 synthesis path| 6315-89-5 SDS| 6315-89-5 COA| 6315-89-5 purity| 6315-89-5 application| 6315-89-5 NMR| 6315-89-5 COA| 6315-89-5 structure
A129054 [27191-09-9]
3-Methoxyaniline hydrochloride
Similarity: 0.92
A129054 [27191-09-9]
3-Methoxyaniline hydrochloride
Similarity: 0.92
A209738 [22013-33-8]
2,3-Dihydrobenzo[b][1,4]dioxin-6-amine
Similarity: 0.93
A129054 [27191-09-9]
3-Methoxyaniline hydrochloride
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