1-amino-2-naphthonitrile

The dried 2 L reactor to nitrogen under ethyl cyano acetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2 g (0.824 mol), dimethylformamide 920 mL dissolved after 10 °C It was stirred for 20 minutes .Then into a 1-nitro-naphthalene 92 g (412 mol) the reaction was stirred for 4 hours at 60 ° C. After the reaction solvent was concentrated into a 10percent sodium hydroxide aqueous solution 600 mL was stirred under reflux for 1 hour. The solid was filtered by a column chromatography with methylene chloride and heptane to give the compound 50 g (yield: 60percent) represented by the [intermediate 1-a].2L reactor with ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g(0.453 mol), potassium hydroxide 46.2 g (0.824 mol), and dimethylformamide 920 mLwas added and then 10 ° C 20 min It was stirred. 1- Put the nitro naphthalene 92 g(412 mol) to the reactor and stirred for 4 hours at 60 ° C. Concentration of the solventin the reaction product and then into a 10percent sodium hydroxide aqueous solution 600 mLwas stirred under reflux for 1 hour. The solid was filtered by a column chromatographywith methylene chloride and heptane to give the general formula 6-a 50 g (yield 60percent).The dried 2 L reactor to nitrogen under ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2 g (0.824 mol), dimethylformamide 920 mL dissolved after 10 in the mixture was stirred for 20 minutes. Then into a 1-nitro-naphthalene 92 g (412 mol) to the reaction and the mixture is stirred for 4 hours at 60 . After completion of the reaction the solvent was concentrated, and a 10percent sodium hydroxide aqueous solution 600 mL is stirred under reflux for 1 hour . The solid was filtered by a column chromatography with methylene chloride and heptane to give the compound 50 g (yield: 60percent) represented by Formula 3-a].The dried 2 L reactor was purged with nitrogen, and then 139.8 g (1.236 mol) of ethyl cyanoacetate, 29.5 g (0.453 mol) of potassium cyanide, 46.2 g (0.824 mol) of potassium hydroxide, After dissolving in 920 mL of dimethylformamide, Stir for 20 minutes.92 g (412 mol) of 1-nitronaphthalene was added and the mixture was heated at 60 DEG C Stir for 4 hours.After completion of the reaction, the solvent is concentrated, 600 mL of a 10percent sodium hydroxide aqueous solution is added, and the mixture is refluxed with stirring for 1 hour.The solid was filtered and separated by column chromatography to give 50 g of intermediate 13-a. (Yield: 60percent)The dried 2 L reactor to nitrogen under ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2 g (0.824 mol), dimethylformamide 920 mL dissolved after 10 in the mixture was stirred for 20 minutes. Then into a 1-nitro-naphthalene 92 g (412 mol) to the reaction and stirred for 4 hours at 60 . After the reaction solvent was concentrated into a 10percent sodium hydroxide aqueous solution 600 mL is stirred at reflux for 1 hour. The solid was filtered by a column chromatography with methylene chloride and heptane to give the compound 50 g (yield: 60percent) represented by Formula 3-a].A dried 2 L reactor was charged with 139.8 g (1.236 mol) of methyl cyanoacetate, 29.5 g (0.453 mol) of potassium cyanide, 46.2 g (0.824 mol) of potassium hydroxide, dissolve in 920 mL of dimethylformamide and stir at 10 °C for 20 minutes. 92 g (412 mol) of 1-nitronaphthalene is then added to the reaction mixture and stirred at 60 ° C for 4 hours.After completion of the reaction, the solvent is concentrated, 600 mL of a 10percent sodium hydroxide aqueous solution is added, and the mixture is refluxed with stirring for 1 hour.The solid was filtered and subjected to column chromatography with methylene chloride and heptane to obtain 50 g (yield 60percent) of the compound represented by [Intermediate 3-a].1-nitro-naphthalene 97 g (0.56 mol), methyl cyanoacetate 166.5 g (1.68 mol), potassium cyanide, 40.1 g (0.62 mol) into potassium hydroxide 62.9 g (1.12 mol) was stirred. Then add 970 mL of dimethylformamide was stirred overnight at 60° C . After concentrated under reduced pressure to remove the solvent at room temperature and add 500 mL 10percent aqueous sodium hydroxide solution was refluxed for about one hour. After extracted with ethyl acetate and then separated by column chromatography it was recrystallized from toluene and heptane to obtain <9-a> 50.8 g (yield: 54percent).1-nitro-naphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62mol), potassium hydroxide (62.9 g, 1.12 mol) and dissolved in dimethylformamide (970 mL) and the mixture was stirred overnight at 60°C. After concentrated under reduced pressure to remove the solvent at room temperature into a 500 mL 10percent aqueous sodium hydroxide solution was refluxed for about one hour. After extraction with ethyl acetate and separated by column chromatography and recrystallized from toluene-heptane to give the Sub 2-2-1 50.8 g (yield: 54percent).97 g (0.56 mol) of 1-nitronaphthalene, 166.5 g (1.68 mol) of methyl cyanoacetate, 40.1 g (0.62 mol) of potassium cyanide, 62.9 g (1.12 mol) of potassium hydroxide, And the mixture was stirred.Dimethylformamide 970 mLAnd the mixture was stirred overnight at 60 ° C.After the solvent was removed by concentration under reduced pressure at room temperature, 10percent500 mL of an aqueous solution of sodium hydroxide was added and the mixture was refluxed for about 1 hour.After separation by column chromatography, recrystallization from toluene and heptane gave 50.8 g of intermediate 4-a. (Yield: 54percent)In a 2-L reactor, ethyl cyanoacetate (139.8 g, 1.236 mol), potassium cyanide (29.5 g, 0.453 mol), and potassium hydroxide (46.2 g, 0.824 mol) were dissolved together in dimethylformamide (920 mL) and then stirred at 10° C. for 20 min. To the reactants was added 1-nitronaphthalene (92 g, 412 mol), followed by stirring at 60° C. for 4 hours. The solvent was concentrated and an aqueous 10percent sodium hydroxide solution (600 mL) was added before stirring under reflux for one hour. Following filtration, purification by column chromatography afforded the compound of Chemical Formula 7-a as a solid (50 g): yield 60percentTo a 2 L reactor was added ethyl cyanoacetate (139.8 g, 1.236 mol)Potassium cyanide (29.5 g, 0.453 mol), Potassium hydroxide (46.2 g, 0.824 mol), After dissolving in 920 mL of dimethylformamide, the mixture was stirred at 10 ° C for 20 minutes.1-Nitronaphthalene (92 g, 412 mol) was added to the reactionAnd the mixture was stirred at 60 ° C for 4 hours.The solvent is concentrated, 600 mL of a 10percent sodium hydroxide aqueous solution is added, and the mixture is refluxed with stirring for 1 hour. The solid was filtered and subjected to column chromatography with methylene chloride and heptane to obtain [intermediate 7-a]. (50 g, 37percent).The dried 2 L reactor containing the nitrogen to the reactor ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2g (0.824 mol), dimethylformamide 920 mL dissolved after and stirred at 10 for 20 minutes. Then into a 1nitronaphthalene92 g (412 mol) and stirred for 4hours at 60 . After the reaction solvent was concentrated into a 10percent sodium hydroxide aqueous solution 600 mL is stirred at reflux for 1 hour. The solid was filtered and separated by column chromatography to give the 6-a 50 g. (60percent yield)2 L reactor under nitrogen to ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453mol), potassium hydroxide 46.2 g (0.824 mol), 920 mL of dimethylformamide at dissolved after 10°C and stirred for 20 minutes. Then into a 1-nitro-naphthalene 92 g (412 mol) to the reaction and stirred for 4 hours at 60 °C . After the reaction solvent was concentrated into a 10percent sodium hydroxide aqueous solution 600 mL is stirred at reflux for 1 hour. The solid was filtered to give the compound [Intermediate 13-a] 50 g (yield: 60percent) by column chromatography with methylene chloride and heptaneIn a reactor, 1-nitronaphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62 mol), and potassium hydroxide (62.9 g, 1.12 mol) were stirred together. To the reactants was added dimethylformamide (970 mL), followed by stirring at 60° C. overnight. The solvent was removed by vacuum concentration at room temperature, after which a 10percent sodium hydroxide solution (500 mL) was added and refluxed for about 1 hr. Recrystallization in toluene and heptane subsequent to separation through column chromatography afforded [Intermediate 7-a] (50.8 g): yield 75percent.2L reactor with ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g(0.453 mol), potassium hydroxide 46.2 g (0.824 mol), and dimethylformamide 920 mLwas added and then 10 ° C 20 min It was stirred. 1- Put the nitro naphthalene 92 g(412 mol) to the reactor and stirred for 4 hours at 60 ° C. Concentration of the solventin the reaction product and then into a 10percent sodium hydroxide aqueous solution 600 mLwas stirred under reflux for 1 hour. The solid was filtered by a column chromatographywith methylene chloride and heptane to give the general formula 6-a 50 g (yield 60percent).In a reactor, 1-nitronaphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62 mol), and potassium hydroxide (62.9 g, 1.12 mol) were stirred together. To the reactants was added dimethylformamide (970 mL), followed by stirring at 60 C. overnight. The solvent was removed by vacuum concentration at room temperature, after which a 10% sodium hydroxide solution (500 mL) was added and refluxed for about 1 hr. Recrystallization in toluene and heptane subsequent to separation through column chromatography afforded [Intermediate 7-a] (50.8 g): yield 75%.

Molecular Weight:168.19
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:168.068748264
Monoisotopic Mass:168.068748264
Topological Polar Surface Area:49.8
Heavy Atom Count:13
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes