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CAS No. : | 138113-08-3 | MDL No. : | MFCD08704309 |
Formula : | C13H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PYJMGUQHJINLLD-UHFFFAOYSA-N |
M.W : | 197.23 | Pubchem ID : | 11264068 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.15 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.96 |
TPSA : | 33.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.52 cm/s |
Log Po/w (iLOGP) : | 2.14 |
Log Po/w (XLOGP3) : | 2.8 |
Log Po/w (WLOGP) : | 2.91 |
Log Po/w (MLOGP) : | 2.38 |
Log Po/w (SILICOS-IT) : | 3.3 |
Consensus Log Po/w : | 2.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.19 |
Solubility : | 0.128 mg/ml ; 0.000648 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.15 |
Solubility : | 0.14 mg/ml ; 0.000708 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.7 |
Solubility : | 0.00397 mg/ml ; 0.0000201 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.22 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
91% | With trichlorophosphate; In dichloromethane; N,N-dimethyl-formamide; at 85℃; for 2h; | A mixture of 2-(7-methoxy-1 -naphthyl) acetic acid (100g), Dichloro methane(500 ml). Dimethyl formamide(l ml), thionyl chloride 65.98 g was stirred and heated to 35 to 40 C 1 hr. The solvent was distilled out completely under vacuum. Toluene (800 ml) was added to the residue, ammonia gas was purged at 0-5 C till pH 10-1 1. After the completion of reaction, reaction mixture was heated at 45-50C. Cooled the reaction mass, filtered the solid, washed with toluene. The materials so obtained, Phosphorous oxychloride (85.08 g) and toluene (500 ml) was stirred and heated at 85 C for 2 hrs. The mixture was partitioned between water and toluene. Organic phase was washed with aq. NaHCO3 solution. The solvent was distilled out completely under vacuum. Toluene (50 ml), methanol (200 ml) was added to the residue and cooled 5- 10 C. Filtered the solid and washed with methanol and dried to obtained 2-(7-methoxynaphthyl) acetonitrile (Yield 91 %, HPLC purity 99.5%). |
80% | With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; at 20℃;Cooling with ice; | Reference example 5: The preparation of 7-methoxy-1-naphthaleneacetonitrile 30g 7-methoxy-1-naphthaleneacetamide, 120ml THF and 35.7g triethylamine were added into reaction flask. The mixture was stirred and cooled with external ice saline bath. Trifluoroacetic anhydride was slowly added in drops. After completion of addition, it was stirred for further 15main. Then, the ice bath was removed and stirring was carried out for 2h at room temperature. After completion of the reaction, the reaction solution was evaporated. Subsequently, 200ml water was added and the solution was filtered and dried after stirring for 0.5 hours, to obtain 28g crude product. Recrystallization was carried out using 280ml isopropyl ether and 1.4g activated carbon to obtain 22g refined product with the mp of 82- 84C. The yield is 80%. |
With trifluoroacetic anhydride; In tetrahydrofuran; at 0 - 20℃; | Step 6 (7-Methoxy-naphthalen-1-yl)acetonitrile: At about 0 C., trifluoroacetic anhydride (9.29 g; 44.2 mmol) was added dropwise to a suspension of 2-(7-methoxy-naphthalen-1-yl)acetamide (2.38 g; 11.1 mmol) in anhydrous tetrahydrofuran (30 mL). Under continuous stirring, the mixture was maintained at about 0 C. until 2-(7-methoxy-naphthalen-1-yl)acetamide was no longer detected by TLC. After warming to ambient temperature, the reaction mixture was concentrated and purified by flash column chromatography on silica gel (4*16 cm, ethyl acetate/petrol ether=1:30 elution) to give the title product as a white solid (1.6 g, yield 73% over three steps). 1H NMR (300 MHz, CDCl3) delta 3.98 (s, 3H), 4.09 (s, 2H), 7.09 (d, J=2.1 Hz, 1H), 7.22 (dd, J=9.0, 2.4 Hz, 1H), 7.34 (dd, J=7.8, 7.5 Hz, 1H), 7.55 (d, J=6.9 Hz, 1H), 7.81 (dd, J=8.7, 6.9 Hz, 2H). GC-MS: 197 (M)+. |
5.2 kg | With phosphorus pentoxide; In toluene;Reflux; | 6.0Kg of the compound of the formula (III), 6.5Kg of phosphorus pentoxide and 180L of toluene were added to the reaction vessel, and the reaction was refluxed for 9 to 10 hours, and the temperature was lowered. The reaction solution was washed with 150 L of water, 150 L of sodium hydrogencarbonate solution and 150 L of brine. Dry sodium sulfateDry, filter, and concentrate the filtrate to dryness under reduced pressure. The obtained oil was added 3 L of isopropyl ether, stirred at room temperature for 15 to 20 minutes, filtered, and the filter cake was blast dried for 6 to 8 h to give the compound of formula (IV): 5.2 Kg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogen; sodium hydroxide; In methanol; water; at 30℃; under 3000.3 Torr; | In a 10L reactor compound of formula II (230 g), methanol (3,7 L), NaOH solution ((123,3) g NaOH is diluted in 460mL water) and Raney Nickel (41 ,193 g) is charged. Reaction mixture is stirred at 30°C and 4 bar hb and monitored with HPLC. After reaction is done, it is filtered and solvent is evaporated. To concentrate is added toluene (4,25 L) and water (2,13 L), mixed and separated. To organic phase water is added (2,13 L), pH is adjusted to 2 with 37 percent HCI, and phases are separated. To water phase fe/f-butyl methyl ether (2,13 L) is added and pH is adjusted to 10 with 40 percent NaOH. Further organic phase is concentrated, ethanol (230 mL) is added, heated to 50°C then 4 M HCI in ie/f-butyl methyl ether (355 mL) and ie/f- butyl methyl ether (920 mL). White precipitate started to obtain. Suspension is cooled to room temperature, filtered, washed with ie/f-butyl methyl ether and dried. Product is white solid (256,2, yield 92percent). |
90% | A mixture of 2-(7-methoxynaphthyl) acetonitrile (100g), methanol (800 ml), aq. sodium hydroxide (30.42 g sodium hydroxide in 100 ml water), 20 g of Raney Ni stirred in hydrogen atmosphere (apply H2 gas up to 10 kg) at 25 to 30 °C for 2-3 hrs. Filtered the reaction mixture, distilled out solvent completely under vacuum. IPA is added to the residue and heated at 50 to 55 °C, IPA HCI added at 50 to 55 °C and stirred for one hour. Cooled the reaction mixture at 10-15°C, filtered the solid, washed with IPA and dried. There was thus obtained 2-(7-methoxynanphthyl)ethanamine hydrochloride (Yield 90percent, HPLC purity 99.5 to 99.9 percent) | |
83% | Example 2: Preparation of 2-(7-methoxy-l-naphthyi)ethanamine hydrochloride of Formula (D) Methanol (500 ml) was added to an autoclave with 1 Kg/cm2 pressure of Ammonia gas at 10°C to 15°C and stirred for 1 hour followed by addition of (7-methoxy-l- naphthyl)acetonitrile of Formula (C) (70 g). Raney Nickel (14 g) was added and 5.0 Kg/cm2 pressure of Hydrogen gas was applied at 15°C to 25°C. The reaction was heated to 50°C to 55°C. The reaction mass was filtered and treated with ethyl acetate (500 ml) at 25°C to 35°C and cooled to 0°C to 5°C followed by addition of Con. HCI acid and maintained for 1 hour. The reaction mass was filtered and washed with chilled ethyl acetate (2 X 50 ml) afforded 2-(7-methoxy- l-naphthyl)ethanamine hydrochloride of formula (D) Yield - 83percent |
32% | A solution of (7-methoxynaphthalen-l-yl)acetonitrile (30 g) in methanol (150 mL) and aqueous ammonia (15 mL) was treated with hydrogen gas (3 Kg) in the presence of Raney nickel (45 g) at 40°C. After completion of the reaction, the reaction mixture was filtered through a Hyflo®. The filtrate was concentrated under vacuum (200-220 mbar) at 45°C to 50°C to obtain a residue. The residue in ethyl acetate (60 mL) was acidified (pH 2) with concentrated hydrochloric acid (10 mL to 15 mL) at 10°C to 15°C to obtain a solid. The solid was dried under vacuum (5-10 mbar) at 45°C to 50°C over 10 to 15 hours to get the title product.Yield (w/w): 32percent | |
32% | A solution of <strong>[138113-08-3](7-methoxynaphthalen-1-yl)acetonitrile</strong> (30 g) in methanol (150 mL) and aqueous ammonia (15 mL) was treated with hydrogen gas (3 Kg) in the presence of Raney nickel (45 g) at 40° C. After completion of the reaction, the reaction mixture was filtered through a Hyflo®. The filtrate was concentrated under vacuum (200-220 mbar) at 45° C. to 50° C. to obtain a residue. The residue in ethyl acetate (60 mL) was acidified (pH 2) with concentrated hydrochloric acid (10 mL to 15 mL) at 10° C. to 15° C. to obtain a solid. The solid was dried under vacuum (5-10 mbar) at 45° C. to 50° C. over 10 to 15 hours to get the title product. Yield (w/w): 32percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(7-Methoxy-naphth-1-yl)acetonitrile (20 g) is dissolved in 150 ml of anhydrous tetrahydrofuran. Sodium hydride (202.8 mmol) is added at ambient temperature, and the mixture is refluxed for 30 minutes. Dimethyl carbonate (12 ml) is added with caution, and the reaction mixture is refluxed for 30 minutes. The mixture is poured into ice-cold water, and the aqueous phase is acidified with 21 ml of 37% hydrochloric acid solution and then extracted twice with 100 ml of ether. The organic phase is washed with water, dried, decoloured and evaporated. The oil obtained is precipitated from ether, and the precipitate formed is filtered off under suction and then recrystallized to yield the title compound in the form of a white solid. Melting Point: 80-82 C. | ||
Methyl cyano(7-methoxy-1-naphthyl)acetate (7-Methoxy-naphth-1-yl)acetonitrile (20 g) is dissolved in 150 ml of anhydrous tetrahydrofuran. Sodium hydride (202.8 mmol) is added at ambient temperature, and the mixture is refluxed for 30 minutes. Dimethyl carbonate (12 ml) is added with caution, and the reaction mixture is refluxed for 30 minutes. The mixture is poured into ice-cold water, and the aqueous phase is acidified with 21 ml of 37% hydrochloric acid solution and then extracted twice with 100 ml of ether. The organic phase is washed with water, dried, decoloured and evaporated. The oil obtained is precipitated from ether, and the precipitate formed is filtered off under suction and then recrystallized to yield the title product in the form of a white solid. Melting point: 80-82 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With ammonia; hydrogen; In ethanol; water; at 60℃; under 228015 Torr; for 12h;Autoclave; | Reference example 6: The preparation of 2-(7-methoxy-1-naphthyl)ethylamine 56g 7-methoxy-1-naphthaleneacetonitrile, 120ml ammonia water, 332ml 95% ethanol, 20g Raney-Ni were added into autoclave. H2 was introduced after vacuuming it. The operation was repeated for 3 times. The reaction was stirred for 12 hours while H2 was introduced and the condition of 300 atm and 60C was maintained. After completion of the reaction, the reaction was kept overnight at room temperature. On the next day, it was vacuumed and N2 gas was introduced. The autoclave was opened up, and the reaction solution was filtered to remove the catalyst. The filtrate was vacuum evaporated until dry to obtain 56g light green oil. The content is measured as 96.95% by HPLC, and the yield is 95%. |
92% | With hydrogen; ammonium hydroxide;nickel; In methanol; at 20℃; under 3102.97 Torr; for 20h; | Step 7 2-(7-Methoxy-naphthalen-1-yl)-ethylamine: At ambient temperature and under a pressurized hydrogen atmosphere (60 psi), a mixture of (7-methoxy-naphthalen-1-yl)acetonitrile (1.6 g; 8.1 mmol), Raney nickel (0.5 g) in methanol (80 mL), and ammonium hydroxide (5 mL) was continuously stirred for about 20 hours. The catalyst was then removed by filtration and the filtrate was concentrated to give the title product as a yellow oil, which was used directly in the next step without further purification (1.5 g, yield 92%). 1H NMR (300 MHz, CD3OD): delta 3.00 (br. s, 2H), 3.20 (br. s, 2H), 3.93 (s, 3H), 7.12 (d, J=8.7 Hz, 1H), 7.24 (m, 3H), 7.63 (d, J=7.8 Hz, 1H), 7.73 (d, J=8.7 Hz, 1H). LC-MS: 202 (M+H)+. |
71.2% | With ammonia; hydrogen; In ethanol; at 45℃; under 15001.5 Torr;Green chemistry; | A hydrogenation reaction vessel was charged with <strong>[138113-08-3](7-methoxy-1-naphthyl)acetonitrile</strong> (10.0 g, 50.7 mmol), added to a 500 ml hydrogenreaction vessel, dissolved in 200 ml of anhydrous ethanol, and 0.95 g of Raney nickel wasadded to thehydrogenation reaction. kettle introducing gaseous ammonia, ammonia gas stream flatstable holding 0.1-5h; 1-5 times and then replaced by hydrogen, a sealed reactor; hydrogenation reactor was placed 45 C, 2.0MPa bar hydrogen pressureand stirred overnight under member; the reaction was monitored by TLC until complete; the reaction solution was decanted, suction filtered, rinsed with a little 95% ethanol; filtrate concentratedsolution has a pH, and dissolved in ethyl acetate, hydrochloric acid gas was introduced, the control of the mother liquor is 8.0 to 9.0, a large number of white precipitate heavyprecipitate Suction suspension was filtered off, the filter cake was washed with ethyl acetate, and the filter cake was dried at 50 C. to obtain an off-white solid, ie compound (II) 8.7 g, yield 71.2%, product properties: white powder.Purity: 99.52%. |
With ammonia; hydrogen;nickel; In ethanol; water; at 40℃; under 22502.3 Torr; | There are introduced into a 1100 litre reactor 80.0 kg of the compound obtained in Step B, 24.0 kg of Raney nickel in ethanol and 170 l of ammonium hydroxide. The mixture is stirred under a hydrogen pressure of 30 bars, then brought to 40 C. When all the starting substrate has disappeared, the solvent is evaporated off, the resulting residue is redissolved in ethyl acetate, and 41.5 l of an 11N hydrochloric acid solution are added. After filtration, the precipitate obtained is washed with ethyl acetate and then dried in an oven to give the title product in a yield of 95.3% and with a chemical purity exceeding 99.5%. Melting point: 243 C. | |
With sodium tetrahydroborate; di-tert-butyl dicarbonate; nickel dichloride; In methanol; for 12h; | A mixture of 2-(7-methoxynaphthalen-1-yl) acetonitrile (compound 2,1.99 g, 10.0 mmol), sodiumborohydride (417mg, 11.0 mmol), nickelchloride(475 mg, 5.0 mmol) and dibutyldicarbonate (0.2 mL) in 20 mL methanol were stirred at room temperature for 12 h, then the reaction was suspended with 20 mL water. The resulting mixture was concentrated under reduced pressure, then 20 mL water was added, extracted with ethyl acetate(20 mL×3), the combined organic layer were concentrated under reduced pressure. After that 10 mL trifluoroacetic acid and 10 mL dichloromethane were added, stirred at room temperature for 4 h and adjust to pH=12, then washed with water (20 mL×3) and compound 3 was obtained after concentrated under reduced pressure. | |
With ammonia; hydrogen; In ethanol; at 30 - 40℃; under 2250.23 - 3000.3 Torr; for 24h;Autoclave; | To the autoclave was charged 30 g of (7-methoxy-1-naphthyl) acetonitrile prepared in Example 19, 7.5 g of Raney nickel,95% ethanol 200ml, ammonia 60ml, autoclave sealed, nitrogen replacement, access to hydrogen,Control the pressure of 0.3-0.4Mpa, temperature 30-40 , holding pressure after 24 hours, cooling, remove the reaction solution, filter recovery Raney nickel, the filtrate evaporated under vacuum (7-methoxy-1-naphthyl) Ethylamine oil;To the oil was added 120 ml of toluene, 25 ml of triethylamine was stirred and dissolved,Control temperature below 30 add acetic anhydride 17ml, and 0-10 incubation reaction 30min,Then, 120 ml of water was added dropwise and cooled to 0-5 C for 2 h. The mixture was filtered and dried to give 31 g of aggamatine, the yield was 83.8% and the HPLC purity was 99.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In hexane; hydrogen; acetic anhydride; ethyl acetate; toluene; | EXAMPLE 20 N-[2-(7-methoxy-1-naphthyl)-2-(methoxycarbonyl)ethyl]acetamide A solution of 0.04 mol of 2-<strong>[138113-08-3](7-methoxy-1-naphthyl)acetonitrile</strong> in 150 cm3 of acetic anhydride in the presence of 5 g of catalyst (Raney nickel) is subjected to a hydrogen pressure of 20.7 bars for 30 hours at a temperature of 60 C. with stirring. After filtration of the catalyst and evaporation of the solvent under vacuum, the residual oil is taken up with 250 cm3 of ethyl acetate. The organic phase is washed with saturated sodium carbonate solution and then with water. After drying over sodium sulfate, it is evaporated to dryness, and the residue is then recrystallized in a toluene/hexane (2:1) mixture to obtain N-[2-(7-methoxy-1-naphthyl)-2-(methoxycarbonyl)ethyl]acetamide Yield: 70% Melting point: 118-120 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20℃; under 15.0015 Torr; for 6h;Green chemistry;Catalytic behavior; | In 250 ml of the pressure cooker, added 100 ml of methylene chloride, 10 g (0.05 mole) 7-methoxy-3,4-dihydronaphthalenylacetonitrile, 1.15 g DDQ (0.005 mole). Place 2 kPa pressure of oxygen. Stir at room temperature and react for around 6 hours. the reaction is not further absorb oxygen, reaction stops, the reaction liquid is poured into 50 ml of saturated sodium bicarbonate solution washing, the organic layer then 50 ml of water washing, concentrating the organic layer, the residue with ethanol - water (volume ratio) 50:50 re-crystallization, to obtain the product 7-methoxynaphthalenylacetonitrile 9.4 g, purity 99.2%, yield 95%. |
93% | With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20℃; under 15.0015 Torr; for 5h; | Add 150 ml of dichloromethane to a 500 ml pressure cooker, 19.9 g (0.1 mol) of 7-methoxy-3,4-dihydronaphthaleneacetonitrile, 1.15 g DDQ (0.005 mol), oxygen at a pressure of 2 kPa, The reaction was stirred at room temperature for about 5 hours, the reaction did not further absorb oxygen, the reaction was stopped, The reaction solution was poured into 100 ml of saturated sodium bicarbonate solution, The organic layer was washed with 100 ml of water, the organic layer was concentrated, The residue was recrystallized from 50 ml of ethanol-water = 4: 1, The product was prepared from 18.3 g of 7-methoxynaphthalonitrile, 98.5% purity and 93% yield. |
93% | With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20℃; under 15.0015 Torr; for 5h; | As shown in Figure 2 Preparation of agomelatine important intermediates 7-methoxy naphthalene acetonitrile method.In a 500 ml pressure cooker was added 150 ml of methylene chloride, 2-cyanoacetic acid, 19.9 g (0.1 mol) of 7-methoxy-3,4-dihydronaphthaleneacetonitrile and 2.5 g of DDQ (0.005 mol) were introduced into a 2 kPa pressure oxygen and stirred at room temperature for about 5 hours. The reaction did not further absorb oxygen , The reaction was stopped, the reaction solution was poured into 100 ml of saturated sodium bicarbonate solution was washed,The organic layer was washed with 100 ml of water, the organic layer was concentrated,The residue was recrystallized from 50 ml of ethanol-water = 4: 1,18.3 g of product 7-methoxynaphthalene acetonitrile, purity 98.5%Yield 93%. |
93% | With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20℃; under 15.0015 Torr; for 5h; | A method for synthesizing 7-methoxynaphthalene acetonitrile as shown in FIG. 2. In a 500 ml pressure cooker was added 150 ml of methylene chloride,19.9 g (0.1 mol) of 7-methoxy-3,4-dihydronaphthaleneacetonitrile,1.15 grams DDQ (0.005 mole),Into the 2kPa pressure of oxygen,The reaction was stirred at room temperature for about 5 hours,The reaction did not further absorb oxygen, the reaction was stopped,The reaction solution was poured into 100 ml of saturated sodium bicarbonate solution, the organic layer was washed with 100 ml of water,The organic layer was concentrated and the residue was recrystallized from 50 ml of ethanol-water = 4: 1,The product 7-methoxy-naphthalene acetonitrile 18.3 g, purity 98.5%, yield 93%. |
91% | With allyl methacrylate;5%-palladium/activated carbon; In toluene;Heating / reflux; | There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After removal of the toluene by evaporation, the resulting solid residue is recrystallized from an ethanol/water (80/20) mixture to give the title product in a yield of 91% and with a chemical purity exceeding 99%. Melting point: 83 C. |
91% | With allyl methacrylate;palladium on activated charcoal; In toluene;Heating / reflux; | There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After removal of the toluene by evaporation, the resulting solid residue is recrystallized from an ethanol/water (80/20) mixture to give the title product in a yield of 91% and with a chemical purity exceeding 99%. Melting point: 83 C. |
91% | With allyl methacrylate;5%-palladium/activated carbon; In toluene;Heating / reflux; | There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After removal of the toluene by evaporation, the resulting solid residue is recrystallized from an ethanol/water (80/20) mixture to give the title product in a yield of 91% and with a chemical purity exceeding 99%. Melting point: 83 C. |
91% | With allyl methacrylate;5% Pd(II)/C(eggshell); In toluene;Reflux; Industry scale; | Step B: (7-Methoxy-1-naphthyl)acetonitrile There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile dissolved in toluene are added and also 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is monitored by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After evaporating off the toluene, the solid residue obtained is recrystallized from an ethanol/water (80/20) mixture to yield the title product in a yield of 91% and with a chemical purity of more than 99%. Melting point: 83 C. |
91% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; for 2h;Reflux;Product distribution / selectivity; | Example-3: 5 g. (0.02 mol.) of (7-Methoxy-3,4-dihydro-l-naphthyl)acetonitrile, 7.5 g. (0.03 mol.) of 2,3-Dichloro-5,6-dicyano-benzoquinone (DDQ) and 200 ml. of O-xylene or toluene were charged in a clean and dry 4 neck R.B. Flask and heated to reflux temperature for about 2 hrs. The resultant reaction mixture was cooled to about 30C and filtered. The filtrate was washed with 3x25 ml. of 10% w/v sodium hydroxide solution and 2x25 ml. of water. The solvent was distilled completely under vacuum and the resulted solid residue was recrystallized from ethanol/ and water mixture in a ratio of 8:2 to yield 4.5 gr. (91%) of the title compound with a chemical purity 99%. |
65.8% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 25℃; | 2-(7-methoxy-3,4-dihydronaphth-1-yl)acetonitrile(5.44g, 27.30mmol) and DDQ (7.44g, 32.76mmol) in dichloromethane (30 mL) at 25 in The reaction overnight, diluted with 60mL of ethyl acetate, filtered and the filtrate washed with saturated sodium bicarbonate solution (40 mL) and saturated brine (40 mL), dried the organic phase after separation was dried over anhydrous sodium sulfate. Filtered, the filtrate was spin dry, purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 60/1) to give the title compound as a yellow solid (3.54g, 65.8%). |
With sulfur; at 175℃; for 0.166667h;Product distribution / selectivity; | Example 21: Preparation of 2-(7-methoxy-l-naphthyl)acetonitrile (IVa)IV IVa(i) Taken 60gr. of (7-methoxy-3,4-dihydro-l-naphthyl)acetonitrile (IV) in a Hit. RBF. Added 24gr. of sulphur. Then heated to about 175C and stirred for lOmin. at the same temperature. Then cooled to 50-60C.Added 430ml. of 20% aq.ethanol solution and heated to 70-75C.6gr. of carbon treatment was given to the solution. Taken the filterate, cooled to 5- 10C and maintained for 30min. at the same temperature. Filtered the solid and washed with 30ml. of chilled 20%aq.ethanol and dried to furnish 20gr. of the title compound. | |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 10 - 20℃; for 1h; | Example 1: Preparation of (7-methoxy-l-naphthyl)acetonitrile of Formula (C) 7-methoxy- l-tetralone of Formula (A) (200 g), toluene (1000 ml), cyanoacetic acid ( 140 g), benzyl amine (30 g) and formic acid ( 13 g) were added at 25C to 35C and stirred for 20 minutes. The reaction mass was heated to 1 10C to 120C and maintained for 30 to 36 hours. The reaction mass was treated with Sodium hydroxide solution (500 ml) and organic layer (7-Methoxy-3,4-dihydro- l -naphthalenyl)acetonitrile of Formula (B) was taken for the next step. Toluene (1000 ml) and 2,3-Dichloro-5,6-dicyano 1 ,4- benzoquinone (240 g) was added at 25C to 35C. The reaction mass was cooled to 10C to 20C and separated organic layer of compound of Formula (B) was added and maintained for 1 hour. The reaction mass was washed with Toluene (200.0 mL) and treated with Sodium bicarbonate solution (500 ml). The organic layer was treated with charcoal (10 g) and finally treated with ethanol (300 ml) at 25-30C. The reaction mass was heated at 50C to 55C followed by addition of water (200 ml) and cooled to 25C to 30C. The reaction mass was filtered and washed with chilled ethanol (2x50ml) afforded (7-methoxy- 1 -naphthyl)acetonitrile of Formula (C). Yield - 76% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Synthesis of 2-(7-hydroxynaphthalen-1-yl)acetonitrile (11)To a solution of nitrile 10 (0.500 g, 2.5 mmol) in DCM (20 mL) at -78 C. was added BBr3 (0.337 mL, 6.3 mmol, 2.5 eq) with stirring. The reaction mixture was stirred at -78 C. for 1 h then poured into cold (0 C.) CH3OH (100 mL). The resulting solution was concentrated under reduced pressure then dried under high vacuum to yield a brown solid. Purification via automated flash column chromatography (90:10:1-CHCl3:CH3OH:NH4OH) afforded intermediate 11 (218 mg, 48% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With d(4)-methanol; water-d2; potassium carbonate; In tetrahydrofuran; at 20℃; for 5h; | Step 1 d2-(7-Methoxy-naphthalen-1-yl)acetonitrile: Deuterium oxide (17 mL) and d4-methanol (12 mL) were added to a solution of (7-methoxy-naphthalen-1-yl)acetonitrile (4 g, 20.3 mmol) and potassium carbonate (4.2 g; 30.4 mmol) in tetrahydrofuran (30 mL). The mixture was maintained at ambient temperature for about 5 hours. The solvents were then removed in vacuo to give a brown solid, which was then dissolved in ethyl acetate (100 mL). Standard extractive workup afforded the desired compound as a brown solid (3.80 g, yield 95%). 1H NMR (300 MHz, CD3OD) delta 3.97 (s, 3H), 7.08 (d, J=1.8 Hz, 1H), 7.23 (dd, J=9.0, 2.1 Hz, 1H), 7.34 (dd, J=8.1, 7.2 Hz, 1H), 7.56 (d, J=7.2 Hz, 1H), 7.80 (d, J=6.9 Hz, 1H), 7.82 (d, J=8.7 Hz, 1H); GC-MS: 199 (M)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With hydrogen;Raney nickel; In ethanol; water; at 70℃; under 22502.3 Torr; | Step C: N-[2-(7-Methoxy-1-naphthyl)ethyl]acetamide There are introduced into an 8 litre reactor 136 g of Raney nickel, 2.06 litres of ethanol and 0.23 litre of water. Whilst stirring at 70 C. and under 30 bars of hydrogen, the compound obtained in Step B (0.8 kg), dissolved in acetic anhydride (2.4 litres), is added slowly. At the end of the addition, the reaction mixture is stirred for 1 hour under hydrogen at 30 bars; the reactor is then subjected to decompression and the liquors are filtered. After concentrating the mixture, the residue is crystallized from an ethanol/water 35/65 mixture to yield the title product in a yield of 89% and with a chemical purity of more than 99%. Melting point: 108 C. |
89% | With hydrogen; In ethanol; water; at 70℃; under 22502.3 Torr; | The reaction was carried out on a larger batch in order to optimise the yield obtained: 136 g of Raney nickel, 2.06 L of ethanol and 0.23 L of water are introduced into an 8 L reactor. Whilst stirring at 70 C. and under 30 bars of hydrogen, the compound obtained in Step D (0.8 kg) dissolved in acetic anhydride (2.4 L) is slowly added. At the end of the addition, the reaction mixture is stirred for 1 hour under hydrogen at 30 bar, the reactor is then decompressed and the liquors are filtered. After concentration of the mixture, the residue is crystallised from a mixture of ethanol/water 35/65 to yield the title product in a yield of 89% and with a chemical purity greater than 99%. Melting point: 108 C. |
89% | With hydrogen; In ethanol; water; at 70℃; under 22502.3 Torr; for 1h; | 136 g of Raney nickel, 2.06 L of ethanol and 0.23 L of water are introduced into an 8-L reactot Whilst stirring at 70 C. and under 30 bars of hydrogen, the compound obtained in Step D above (0.8 kg) dissolved in acetic anhydride (2.4 L) is added slowly. When the addition is complete, the reaction mixture is stirred for 1 hour under hydrogen at 30 bars, and then the reactor is depressurised and the liquors are filtered. Afier concentration of the mixture, the residue is crystallised from a mixture of ethanol/water 35/65 to yield the title product in a yield of 89% and with a chemical purity greater than 99%.10075] Melting point: 108 C. ?H NMR spectroscopic analysis (CD3OD, 300.13MHz, oe in ppm): 8.21 (bs, 1H); 7.74 (d, J=8.9 Hz, 1H); 7.65 (d, J=8.0 Hz, 1H); 7.52 (d, J=2.5 Hz, 1H); 7.31-7.2 (m, 2H); 7.11 (dd, J=8.9 and 2.5 Hz, 1H); 3.96 (s, 3H); 3.52-3.44 (m, 2H); 3.23-3.18 (m, 2H); 1.94 (s, 3H). ?3C NMR spectroscopic analysis (CD3OD, 75.5 MHz, oe in ppm): 173.4 (s); 159.4 (s); 135.1 (s); 134.6 (s); 131.2 (d); 130.8 (s); 128.2 (d); 127.9 (d); 124.2 (d); 119.3 (d); 103.2 (d); 55.9 (q); 41.4 (0; 34.2 (0; 22.6 (q). |
In 10L reactor 2-(7-methoxynaphthalen-1 -yl)acetonitrile (750g), methanol (6,3L), NaOH solution (228g NaOH is diluted in 750ml_ water) and 134g of Raney-Nickel is charged. Reaction mixture is stired at 30C and 4 bar H2 and monitored with HPLC. After reaction is done, it is cooled to 15C and acetic anhydride (750mL) is added and warmed to 25C. Reaction is monitored with HPLC. Once the reaction is finished it is filtered, solvent evaporated, than ethyl acetate (5L) is added and organic phase is extracted with water (5L). Solvent is evaporated to obtain agomelatine of 96,4% HPLC purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In water; dimethyl sulfoxide; at 65℃; for 3h; | Step C: (7-Methoxy-1-naphthyl)acetonitrile To a solution of the compound obtained in Step B (100 g) in 30 mug of DMSO and 5 ml/g of water there are added 1.2 equivalents of potassium cyanide (37.8 g). The reaction mixture is heated to 65 C. and maintained at 65 C. for 3 hours. After returning to ambient temperature, an MTBE/water (1/1) binary system is added to the mixture. The aqueous phase is removed. The organic phase is washed several times with water and then with saturated NaCl solution. The solvents are distilled off and the title compound is obtained in a quantitative yield. Melting point: 83 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; for 6h;Reflux; | Compound 1 (<strong>[138113-08-3]2-<strong>[138113-08-3](7-methoxynaphthalen-1-yl)acetonitrile</strong></strong>(1.01 mmol), and sodium azide (40.4 mmol) were dissolved in dry dimethyl formamide as solvent. To this ammonium chloride (40.4 mmol) was added slowly and the reaction was heated to reflux for about 6 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature. A solution of one molar HCl (50 mL) was added slowly until get a solid was collected, which was washed with water and then dried. The crude solid was re-crystallized with n-hexane to obtain a light brown colored solid.Yield: 65%; mp: 178-180 C (decomposition). I R (KBr,cm-1): 1246, 1508, 1627, 2829, 2875, 3024, 3115; 1H-NMR(DMSO-d6) delta: 3.85 (s, 3H, -OCH3), 4.71 (s, 2H, -CH2), 7.18-7.21 (dd, J=9.2 Hz, 2.4 Hz, 1H, Ar-H), 7.31-7.38 (m, 3H,Ar-H), 7.80-7.82 (d, J=8.0 Hz, 1H, Ar-H), 7.86-7.88 (d, J=9.2, 1H, Ar-H), 16.18(br, s, 1H, -NH); MS (EI): m/z = 240.8[M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Example 4(A): Preparation of 2-(7-Methoxynaphthalen- 1 -YDEthanamine Carbon Dioxide Adduct Formula VIII A solution of (7-methoxynaphthalen- 1 -yl)acetonitrile (5 g) in methanol (20 mL) and aqueous ammonia (10 mL) was treated with hydrogen gas (2 Kg) in the presence of Raney nickel (2.5 g) at 40C. After completion of the reaction, the reaction mixture was filtered through Hyflo. The filtrate was concentrated under vacuum to obtain a residue. The residue was dissolved in toluene (30 mL), and was purged with carbon dioxide gas (for at least 4 hours to 5 hours) at 10C to 15C to obtain a solid. The solid was dried under vacuum at 30C to 35C for 10 hours to 15 hours. Yield (w/w): 81% Mass = 202.4 (M+l) H NMR (CDC13): 2.31 (bs, NH2), 3.10-3.13 (m, 2H), 3.17-3.20 (m, 2H), 3.92 (s, 3H), 7.15 (dd, 1H), 7.20-7.32 (m, 3H), 7.65 (d, 1H), 7.75 (d, 1H) XRD (degrees 2Theta) = 5.00, 10.07, 14.30, 15.14, 16.03, 16.80, 17.36, 18.08, 19.01, 20.29, 22.06, 22.72, 22.99, 24.43, 25.89, 26.70, 26.97, 28.92, 35.83 and 38.37 (± 0.2) 2Theta The X-ray powder diffractograms (XRPD) were recorded on a PANalytical X'pert Pro instrument. The measurements were done using CuKa radiation at 45kV. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With chloranil; In toluene; at 80℃; for 2.5h; | To a solution of TCQ (615 mg, 2.5 mmol) in toluene (1.5 mL) heated to 80 C. there is added the compound obtained in Step C (462 mg, 2.3 mmol) dissolved in toluene (3.5 mL). The mixture is then refluxed for 2.5 hours and is then diluted with water and extracted with petroleum ether. The organic phase is washed with NaOH solution (30% by weight) and with water and is then dried over MgSO4, filtered and concentrated under reduced pressure. The residue is purified by column chromatography (petroleum ether-ethyl acetate: 80-20) to yield the title product in solid form in a yield of 61%. HRMS (EI, m/z) Calc. for C13H11NO: 197.0841; found: 197.0838. |
Tags: 138113-08-3 synthesis path| 138113-08-3 SDS| 138113-08-3 COA| 138113-08-3 purity| 138113-08-3 application| 138113-08-3 NMR| 138113-08-3 COA| 138113-08-3 structure
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