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CAS No. : | 119-68-6 | MDL No. : | MFCD00002424 |
Formula : | C8H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WVMBPWMAQDVZCM-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 67069 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 42.71 |
TPSA : | 49.33 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) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 2.03 |
Log Po/w (WLOGP) : | 1.24 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 0.89 |
Consensus Log Po/w : | 1.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -2.33 |
Solubility : | 0.711 mg/ml ; 0.0047 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.69 |
Solubility : | 0.306 mg/ml ; 0.00202 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.19 |
Solubility : | 0.972 mg/ml ; 0.00643 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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 |
---|---|---|
84% | With acetic acid; sodium hydroxide In water at 75℃; for 4 h; | Sodium cyanate (28mmol) in water (25mL) was added to a solution of N-methyl anthranilic acid (20mmol) and acetic acid (0.2mL) in water (50mL) with stirring. When the temperature of the reaction mixture reached 40°C, NaOH was added in portions till the reaction temperature reach to 75°C. Stirring was continued without cooling for 4h, after which the crystals were filtered off and dissolved in boiling water (50mL). The solution was acidified with 50percent H2SO4 to pH 1–2. The precipitated crystals were filtered off, washed with water and recrystallized from 50percent acetic acid to give compound 2 (2.92g, 84percent); m p 278°C [24]. |
77% | Stage #1: With acetic acid In water at 50℃; for 1 h; Stage #2: at 50 - 80℃; |
Sodium cyanate (30.15 g, 0.46 mol) was added to a slurry of N- methylanthranilic acid (50.0 g, 0.33 mol) in water (1 .75 L) and acetic acid (3.3 mL). The reaction mixture was heated to 50 °C for 1 h. The solution was slowly basified by the addition of sodium hydroxide (exothermic). The resulting solution was heated to 80 °C and stirred overnight. The reaction mixture was cooled to 0 °C and the resultant precipitate collected by filtration. The solid was dissolved in boiling water (200 mL) and acidified with cone, sulfuric acid to pH 2. The slurry was cooled to room temperature and filtered. The solid was dried in a vacuum oven to give 1 -methylquinazoline-2,4(1 H,3H)-dione (53 g, 0.30 mol, 77percent).1 H NMR (300MHz, DMSO-d6) δ = 1 1 .54 (br. s., 1 H), 8.00 (d, J = 7.7 Hz, 1 H), 7.77 (t, J = 7.9 Hz, 1 H), 7.43 (d, J = 8.6 Hz, 1 H), 7.28 (t, J = 7.5 Hz, 1 H), 3.33 (s, 3H) |
69% | With acetic acid; sodium hydroxide In water at 40 - 75℃; for 4 h; | 2-(Methylamino)benzoic acid (4.50 g, 0.0300 mol) and acetic acid (0.3 mL) were dissolved in water (158 mL), a solution of sodium isocyanate (2.76 g, 42.0 mmol) in water (54 mL) was added slowly at room temperature. The reaction mixture was heated to 40°C and added with sodium hydroxide (34.8 g, 0.870 mol). The temperature was raised to 75°C and the reaction solution was stirred for 4 hours, cooled to room temperature, filtered and the filter cake was dissolved in boiling water (10 mL). The system was adjusted to pH 1-2 with 50percent sulfuric acid solution (15 mL), filtered and the filter cake was washed with a small amount of water (3 mL) and dried under reduced pressure to give 1-methylquinazoline-2,4-dione (3.64 g, as a yellow solid) with a yield of 69percent. 1H NMR: (400 MHz, DMSO-d6) δ 11.55(s, 1H), 8.00(d, J = 8.0 Hz, 1H), 7.78(t, J = 8.0 Hz, 1H), 7.42(d, J = 8.0 Hz, 1H), 7.28(t, J = 8.0 Hz, 1H), 3.44(s, 3H). MS-ESI calcd. [M + H]+ 177, found 177. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.3% | at 150℃; for 5 h; | Urea (460 mmol) was heated to melt, then 2-methylaminobenzoic acid (46 mmol) was added. The mixture was stirred for 5 h at 150 °C and then cooled to below 100 °C. Water (70 mL) was added to quench the reaction. The precipitated was collected and recrystallized in a mixed solution of acetone (10 mL) and water (100 mL) to afford compound 1 as a white powder (5.25 g, 64.3percent); mp 278-279 °C; 1H NMR (DMSO-d6) δ (ppm): 3.43 (s, 3H), 7.26 (t, J = 12 Hz, 1H), 7.41 (d, J = 12 Hz, 1H), 7.75 (t, J = 15 Hz, 1H), 7.98 (d, J = 6 Hz, 1H), 11.54 (s, 1H). ESI-MS (m/z): 177 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | for 20 h; Inert atmosphere; Reflux | Concentrated sulfuric acid (2 mL, 37 mmol, 98percent) was added to a stirred solution of 2-(methylamino)-benzoic acid 7 (1.1 g, 7.5 mmol) in anhydrous ethanol (16.5 mL). The solution was refluxed for 20 hours, or until the reaction was complete. The solvent was removed under reduced pressure and the residue was re-dissolved in water (20 mL) and neutralised with sodium hydroxide (5 M). The aqueous phase was extracted with chloroform (3 x 20 mL), the organic layers were combined, washed with brine (40 mL), dried over anhydrous magnesium sulfate and the solvent evaporated to yield a brown oil 8 in quantitative yield (1.3 g, 7.5 mmol, 100percent). Rf 0.40 (1/10 v/v ethyl acetate/hexane); IR (ZnSe cell, oil) vmax: 3378 (w, aromatic R2NH), 2981, 2906 (w, C-H), 1677 (s, C=O), 1579, 1517 (m, aromatic C=C), 1233 (s, aromatic R2NH, ester C-O), 1125, 1085 (m, aromatic C=C) cm-1; 1H NMR (300 MHz, d6-DMSO): δ 7.79 (1H, dd, 3J6-5 = 8.1 Hz, 4J6-4 = 1.4 Hz, 6-CH), 7.56 (1H, br, d, 3JNH-10 = 4.2 Hz, NH) 7.40 (1H, ddd, 3J5-6 ~ 3J5-4 = 7.8 Hz, 4J5-3=1.2 Hz, 5-CH), 6.71 (1H, d, 3J3-4 = 8.4 Hz, 3-CH), 6.57 (1H, dd, 3J4-3 ~ 3J4-5 = 7.8 Hz, 4-CH), 4.25 (2H, q, 3J8-9 = 7.02 Hz, 8-CH2-), 2.91 (3H, d, 3J10-NH = 5.1 Hz, 10-CH3), 1.30 (3H, t, 3J9-8 = 7.2 Hz, 9-CH3) ppm; 13C NMR (125 MHz, CDCl3): δ 168.0 (7-C=O), 151.4 (2-C), 133.8 (4-CH), 130.9 (6-CH), 113.6 (5-CH), 110.0 (3-CH), 109.5 (1-C), 59.5 (8-CH2-), 28.8 (10-CH3), 13.7 (9-CH3) ppm; LRMS (+ ESI) m/z: 180 ([M + H]+, 100percent), 162 ([M – C3H5O2 + MeOH + Na + H]+ 56percent), 134 ([M - OCH2CH3]+, 47percent), 130 ([M - (CO2CH2CH3) + Na + H]+, 48percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With lithium aluminium tetrahydride In tetrahydrofuran for 1 h; Heating / reflux | a) Preparation of 2-(N-methylamino)-benzylalcohol [00260] To a suspension of lithium aluminum hydride (0.76 g, 0.02 mol) in dry tetrahydrofuran (40 ml) was added a solution of N-methylanthranilic acid(a) (1.51 g, 0.01 mol) in dry tetrahydrofuran under Ar atmosphere. After refluxing for 1 h, the reaction was quenched by adding ice water (50 ml). The mixture was filtered on a celite pad and thoroughly washed with dichloromethane (50 ml). The organic layer was separated and the water layer was extracted with dichloromethane (50 ml). The combined organic layer was washed with brine (30 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting yellowish oil was purified on a column of silica gel (wakogel. C-200 50 g, eluent n-hexane: ethyl acetate=2:1) to give the title compound(b) as colorless oil (1.18 g, 86percent). 1H-NMR (270 MHz, CDCl3): δ 2.87 (3H, s), 3.00-3.10 (1H, br.s), 4.64 (2H, s), 6.65-6.69 (2H, m), 7.05 (1H, d, J=7.2), 7.23-7.29 (1H, m) |