Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 2801-32-3 | MDL No. : | MFCD00083017 |
Formula : | C10H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DWHMTTROZUHZMC-UHFFFAOYSA-N |
M.W : | 188.18 | Pubchem ID : | 19957914 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.53 |
TPSA : | 58.71 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) : | -5.1 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 3.31 |
Log Po/w (WLOGP) : | 2.45 |
Log Po/w (MLOGP) : | 1.78 |
Log Po/w (SILICOS-IT) : | 0.7 |
Consensus Log Po/w : | 1.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.55 |
Solubility : | 0.0525 mg/ml ; 0.000279 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.22 |
Solubility : | 0.0114 mg/ml ; 0.0000604 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.47 |
Solubility : | 0.0638 mg/ml ; 0.000339 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.7 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid; at 0 - 20℃; for 1.0h; | HNO3 (4.72 mL, 105 mmol) was added dropwise to a mixture consisting of 3-methylquinoline (5.0 g, 35 mmol) and H2SO4 (5 mL) at 0 C., and the reaction mixture was stirred at room temperature for 1 h. The resultant mixture was neutralized to pH 7 with 1 M aq. NaOH, extracted with ethyl acetate (30 mL*3), and the extracts were concentrated under reduced pressure and purified by FCC (petroleum ether: ethyl acetate=100:0 to 50:50) to afford a mixture of compounds 27a and 27a-1 (4 g, 30%). LCMS (ESI): mass calcd. for C10H8N2O2 188.18, m/z found 189.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With arsenic(V) oxide; sulfuric acid; In water; toluene; | 3-Methyl-8-nitroquinoline Sulfuric acid (34 ml, 63.2 g, 645.2 mmol) in water (12 ml) was added to a mixture of arsenic pentoxide (22.26 g, 96.8 mmol) and 2-nitroaniline (22.28 g, 161.3 mmol) and the solids dissolved. The resultant solution was then heated to 100 C. and 2-methyl-2-propene-1,1-diol diacetate (50 g, 290.3 mmol) was added, causing an exothermic reaction which was controlled so as not to exceed 130 C. After the addition of the 2-methyl-2-propene-1,1-diol diacetate, the mixture was heated and stirred at 130 C. for 2 hours. The reaction mixture was then cooled and poured onto ice-water. The resultant mixture was basified with aqueous sodium hydroxide solution (50%) and toluene was then added and the mixture heated to 90 C. for 1 hour. The toluene layer was then decanted off and replaced with more toluene (400 ml). The mixture was then heated and stirred over-night and the toluene decanted. More toluene (400 ml) was then added and the mixture heated and stirred for 2 hours before decanting and combining with the two previous toluene extracts. The combined toluene extracts were dried (MgSO4), filtered and the filtrate evaporated in vacuo to give a dark brown solid. This solid was triturated with diethyl ether, the solid isolated by filtration, pulverised, washed with ether and dried in vacuo at 50 C. for 2 hours to give the solid product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetic acid; ethyl acetate; toluene; | 8-Amino-3-methyl-1,2,3,4-tetrahydroquinoline Platinum oxide (0.375 g) was added to a solution of <strong>[2801-32-3]3-methyl-8-nitroquinoline</strong> (12.47 g, 66.3 mmol) in acetic acid (150 ml) and hydrogenated at 60 psi for 24 hours. The acetic acid solution was filtered through celite to remove the catalyst and then evaporated in vacuo and the residue treated with toluene (150 ml). The toluene was removed in vacuo. More toluene was added and the resultant solution filtered and then evaporated in vacuo. The crude product was then dissolved in ethyl acetate and purified by chromatography on a pad of silica. The ethyl acetate fractions containing product were collected and combined, then washed with aqueous sodium hydrogen carbonate solution (75 ml), dried (MgSO4) and filtered. The filtrate was evaporated in vacuo to give a dark brown oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; In chlorobenzene; | EXAMPLE 1 Preparation of 3-(Bromomethyl)-8-nitroquinoline STR6 A stirred mixture of <strong>[2801-32-3]3-methyl-8-nitroquinoline</strong> (9.5 g, 0.05 mol) in chlorobenzene (75 mL) is heated to 80 C. under nitrogen. A mixture of N-bromosuccinimide (9.0 g 0.05 mol). and 2,2'-azobisisobutyronitrile (0.5 g, 0.003 mol) is added to the reaction mixture. The reaction mixture is held at 80-90 C. for 1 hour. The mixture is washed with water (100 mL) at 60-80 C., cooled to room temperature and filtered to obtained a solid. The solid is washed with chlorobenzene and vacuum dried to give the title product as light-yellow solid (3.9 g mp 121-124 C.) which is identified by 1 H and 13C NMR spectral analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
300 mg | HNO3 (4.72 mE, 105 mmol) was added dropwise to a mixture consisting of 3-methylquinoline (5.0 g, 35 mmol) and H2S04 (5 mE) at 00 C., and the reaction mixture was stirred at room temperature for 1 h. The resultant mixture was neutralized to pH 7 with 1 M aq. NaOH, extracted with ethyl acetate (30 mEx3), and the extracts were concentrated under reduced pressure and purified by FCC (petroleum ether: ethyl acetate=100:0 to 50:50) to afford a mixture of compounds 27a and 27a-1 (4 g, 3 0%). ECMS (ESI): mass calcd. for C,QH8N202 188.18, mlz found 189.0 [M+H]. A mixture of 3-methyl-5-nitroquinoline (27a) and <strong>[2801-32-3]3-methyl-8-nitroquinoline</strong> (27a-1) (3.50 g, 9.30 mmol), MeOH (30 mL) and dry Pd/C (350 mg, 5%) was added to a 500 mL hydrogenation bottle. The mixture was stirred under a H2 (30 psi) atmosphere at room temperature for 16 h. The suspension was filtered though a pad of diatomaceous earth and the pad was washed with MeOH (100 mL). The filtrate was concentrated to dryness under reduced pressure to give crude compound 27b, which was purified by FCC (ethyl acetate:methanol=100:0 to 95:5) to afford compound 27b (300 mg, 20%). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.64 (d, J=1.6 Hz, 1H), 8.30 (s, 1H), 7.37-7.30 (m, 1H), 7.15 (d, J=8.0 Hz, 1H), 6.68 (d, J=7.2 Hz, 1H), 5.83 (s, 2H), 2.46 (s, 3H). |