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CAS No. : | 614-18-6 | MDL No. : | MFCD00006389 |
Formula : | C8H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XBLVHTDFJBKJLG-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 69188 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.32 |
TPSA : | 39.19 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) : | -6.28 cm/s |
Log Po/w (iLOGP) : | 1.87 |
Log Po/w (XLOGP3) : | 1.32 |
Log Po/w (WLOGP) : | 1.26 |
Log Po/w (MLOGP) : | 0.66 |
Log Po/w (SILICOS-IT) : | 1.51 |
Consensus Log Po/w : | 1.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.81 |
Solubility : | 2.32 mg/ml ; 0.0153 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.74 |
Solubility : | 2.73 mg/ml ; 0.018 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.49 |
Solubility : | 0.491 mg/ml ; 0.00325 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
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 |
---|---|---|
87.4% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 h; | Tetrahydro Lithium aluminum (1.24g, 47mmol) dissolved in anhydrous tetrahydrofuran (20mL). After 0.5h at reflux, cooled to room temperature to, and then added dropwise nicotinic acid ethyl ester (2.40g, 16mmol) in anhydrous tetrahydrofuran (15mL ) solution. Was stirred at room temperature for 4h, the end of the reaction was detected by TLC. 50mL of saturated aqueous ammonium chloride solution was added under ice-cooling, remove the excess of lithium aluminum tetrahydride. Filtered off with suction, the filter cake (10mL × 3) and washed with ethyl acetate. (30mL × 3) The mother liquor was extracted with ethyl acetate, the combined ethyl acetate phases were dried over anhydrous magnesium sulfate, filtered and concentrated by column chromatography to give a colorless oil (1.52 g of, yield: 87.4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With hydrazine hydrate monohydrate In methanol at 140℃; for 1 h; Microwave irradiation; Sealed tube | General procedure: A solution of the appropriate ethyl or methyl esters 21a-d (1.0 mmol) in methanol (5 mL) was prepared in a 10 mL CEM microwave vessel. Hydrazine hydrate 50percent (5.0 mmol) was added, the vessel was capped and placed in a microwave reactor and the reaction carried out with the following method in dynamic mode: 140° C, 60 min, 100 W, with high stirring. After completion the reaction mixture was transferred to a round bottom flask and the solvent evaporated under reduced pressure. The crude product was transferred to an Erlenmeyer flask and suspended in dichloromethane, heated at 50° C for 5 min, rapidly vacuum filtered and washed with the same solvent, to obtain the pure product (yield 80-90percent). When the product was found to be still not pure, the purification procedure was repeated. |
78% | With hydrazine hydrate In ethanol for 10.25 h; Cooling with ice; Reflux | Nicotinic acid ethyl ester 4 (1.5g, 10mmol) was dissolved in15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (2g, 40mmol), after the addition was complete, it was stirred at room temperature for 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried andconcentrated to give the desired product 5 (1.1g, 78percent), without purification into the next step. |
12.6 g | With hydrazine hydrate In ethanol for 3 h; Reflux | General procedure: An ethanol (300 ml) suspension of salicylic acid(13.8 g; 0.1 mol) and strongly acidic ion-exchange resin,Amberlyst-15 (5 g) were stirred with refluxing for three days.Insoluble catalyst was separated by filtration, and washed withethanol (3 20 ml). Combined ethanol filtrates were mixed with hydrazine hydrate (20 ml; 20.5 g; 0.4 mol) and refluxed with slowsolvent distillation using the modified Hickman still apparatus(Scheme 3). After 3 h of refluxing, the volume of the reaction mixturewas reduced to about 50 ml and white precipitate started toform. The white suspension was cooled to room temperature andthen left at 5 C for 1 h. Insoluble product was separated by filtration,washed with ice cold ethanol, and dried on air to give pureproduct (13.2 g; 87percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | Stage #1: With n-butyllithium In diethyl ether at -78℃; for 0.25 h; Stage #2: at -78℃; for 2 h; |
n-BuLi (71.3 ml, 1.6 M, 0.114 mol) was added dropwise to the solution of 3-bromo pyridine (15 g, 0.095 mol) in dry diethyl ether (200 ml) at -78° C. and stirred for 15 minutes. A solution of ethyl nicotinate (13 g, 0.095 mol) in dry diethyl ether (50 ml) was added dropwise to the reaction mixture at -78° C. and stirred for another 2 h at the same temperature. Then the reaction was quenched with satd. ammonium chloride and extracted with ethyl acetate. The organic layer was washed with satd. brine, dried over anh. sodium sulfate and concentrated. The crude product was purified on neutral alumina column using (methanol/dichloromethane) to give the sub-title compound (8.5 g, 49percent as brown liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.6% | Stage #1: at 125℃; for 4 h; Large scale Stage #2: at 45 - 60℃; for 1 h; Large scale Stage #3: at 10 - 30℃; for 2.5 h; Large scale |
(A) A mixture of 1.6 kg of ethyl nicotinate,Ethanolamine 1.1kg into the reactor.The reaction was heated to 125 ° C for 4 hours.After completion of the reaction,Cooled to 100 ° C,Vacuum distillation,Vacuum distillation vacuum-0.091MPa distillation temperature rose to 130 ~ 135 when the end of distillation, the reaction solution;(B) The reaction solution can be rapidly cooled to 80 ° C with brine under stirring,And then slowly cooled to 65 ;(C) 1.6 kg of acetone was added dropwise at 60 ° C,After the dropwise addition was continued, the temperature was gradually lowered to 45 ° C,Crystal precipitation,And the mixture was stirred at 45 ° C for 1 hour.(D) continue to cool to 30 ° C,Stir for 1.5 hours,And then continue to cool to 10-15 ,Stirred for 1 hour,And then continue to cool to 0 or so,Stirring crystallization after 1 hour out.Centrifugation,The filter cake,The oven was dried at 50-60 & lt; 0 & gt; C,To obtain 1.70 kg of white N- (2-hydroxyethyl) -nicotinamide,The overall yield was 96.6percentMp 89-91 ° C. |
64% | at 20 - 55℃; for 18 h; | General procedure: For the synthesis of the hydroxylated precursors, ethanolamine (1.5 mmol) was added slowly to the esters (1 mmol) at 55°C and stirred for 3 h. The reaction mixture was stirred at room temperature for 15 h. The residue was purified by silica gel column chromatography (eluent/ethyl acetate/hexane 8:2) or recrystallized from ethyl acetate. The progress of the reaction was monitored by TLC.` |
42% | at 80℃; for 48 h; | Ethyl nicotinate (15.1 g, 100.0 mmol, 1.0 eq.) and Ethanolamine (6.1 g, 100.0 rnrnol, 1.0 eq.) were dissolved in toluene (80 ml_). The reaction mixture was heated to 80 0C and stirred for 48 h. During the reaction the mixture changed into a sticky emulsion. The emulsion was cooled down to room temperature and the lower phase became solid. The upper liquid phase was decanted and the orange solid was crystallised twice, first from ethyl acetate and then from acetone. The crystals were dried under high vacuum at room temperature to give 7.1 g (42 percent) of the product as a white, free flowing powder. The 1 H NMR and the 13C NMR corresponds to the literature (Ogawa, T.; Hatayama, K.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1994, 42 (8) 1579-1589). 1H NMR (CDCI3) δ = 3.60-3.64 (q, 2H), 3.82-3.85 (t, 2H), 4.00 (s, 1H), 7.33-7.39 (m, 2H), 8.10-8.14 (m, 1H), 8.64-8.67 (q, 1 H)1 8.99-9.00 (t, 1 H). 13C NMR (CDCI3) δ = 42.8, 61.5, 123.6, 130.2, 135.5, 147.8, 152.0, 166.4. |
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