Structure of 1-quinolin-2-ylmethanamine
CAS No.: 5760-20-3
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| CAS No. : | 5760-20-3 |
| Formula : | C10H10N2 |
| M.W : | 158.20 |
| SMILES Code : | C1=C2C(=NC(=C1)CN)C=CC=C2 |
| MDL No. : | MFCD09261030 |
| InChI Key : | HGHPGHVNTQSTNM-UHFFFAOYSA-N |
| Pubchem ID : | 3014378 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
* 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 sodium hydroxide;palladium; In water; acetic acid; | a. Imidazo[1,5-a]quinoline A solution of 7.7 g. of 2-cyanoquinoline in 100 ml. of acetic acid is treated with 500 mg. of 5% palladium-on-carbon, and the resulting mixture shaken in a hydrogen atmosphere at room temperature at an initial pressure of 50 psi. When the theoretical amount of hydrogen had been taken up, the catalyst is filtered and the filtrate concentrated in vacuo to a brown oil. Water is added to the residue and rendered basic by the addition of 1N aqueous sodium hydroxide. The product, 2-aminomethylquinoline, is extracted into benzene. The benzene extracts are combined, dried and concentrated to an oil, which is used without further purification. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 21% | General procedure: In an autoclave, 3.40 g of 6-cyano-3,4-dimethylpyridine (25.7 mmol), 0.15 g of Pd/C (water-content=50%), 200 mL methanol and 3.0 mL concentrated hydrochloric acid are placed, stirred at room temperature for 3 hours while pressurizing with hydrogen to 3 atm. The reaction solution was filtered through Celite and the filtrate was concentrated to dryness. This was washed with methanol to give 2.41 g of 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA) hydrochloride (93% yield). This 2-aminomethyl-3,4-dimethylpyridine hydrochloride was treated with an aqueous solution of potassium carbonate to give 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA) quantitatively. | |
| With hydrogenchloride; palladium on activated charcoal; hydrogen; In methanol; water; at 20℃; under 2280.15 Torr; for 3h;Autoclave; | General procedure: In an autoclave, 3.40 g (25.7 mmol) of 6-cyano-3,4-dimethylpyridine, 0.15 g of Pd / C (50% hydrous), 200 mL of methanol and 3.0 mL of concentrated hydrochloric acid are added.The hydrogen was stirred at room temperature under pressure of 3 atm for 3 hours.The reaction solution was filtered through celite, and the filtrate was concentrated to dryness.This was washed with methanol to give 2.41 g (93% yield) of 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2 PICA) hydrochloride.This (2-aminomethyl-3,4-dimethylpyridine hydrochloride was treated with aqueous potassium carbonate solution to quantitatively obtain 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA). |
[ 5760-20-3 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In 1,2-dimethoxyethane; | 6-Amino-2-furan-2-yl-4-[(quinolin-2-ylmethyl)-amino]-nicotinonitrile From trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester and <strong>[5760-20-3]2-(aminomethyl)quinoline</strong> in DME. ES-MS m/e (%): 342 (M+H+, 100). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| palladium; In water; acetic acid; | a. Imidazo[1,5-a]quinoline A solution of 7.7 g. of 2-cyanoquinoline in 100 ml. of acetic acid is treated with 500 mg. of 5% palladium-on-carbon, and the resulting mixture shaken in a hydrogen atmosphere at room temperature at an initial pressure of 50 psi. When the theoretical amount of hydrogen had been taken up, the catalyst is filtered and the filtrate concentrated in vacuo to a brown oil. Water is added to the residue and rendered basic by the addition of 1N aqueous hydroxide. The product, 2-aminomethylquinoline, is extracted into benzene. The benzene extracts are combined, dried and concentrated to an oil, which is used without further purification. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With formic acid; | Following the procedure of Preparation AIII-a, 7.92 g. of <strong>[5760-20-3]2-aminomethylquinoline</strong> is formylated with 50 ml. of 97% formic acid to give 5.97 g. of 2-formamidomethylquinoline, m.p. 108-114 C. | |
| With formic acid; | Following the procedure of Preparation AIII-a, 7.92 g. of <strong>[5760-20-3]2-aminomethylquinoline</strong> is formylated with 50 ml. of 97% formic acid to give 5/97 g. of 2-formamidomethylquinoline, m.p. 108-114 C. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | EXAMPLE 9 Reduction of 2-Cyanoquinoline Using the method of Example 1 gave an 88% yield of 2-quinolinemethanamine by spectroscopic analysis at 4F/mole. Increasing charge passed decreased the yield. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 32% | With triethylamine; In ethanol; at 20℃; for 22h; | General procedure: To a solution of [(1S,2R)-3-[[[3-[(dimethylamino)methylene]-2,3-dihydro-2-oxo-1H- indol-5-yl]sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester 8 (32 mg, 0.050 mmol) in absolute ethanol (1 ml) was added neopentylamine (29 mul, 0.25 mmol). The resulting solution was stirred 22 h and then concentrated in vacuo. The residue was purified on a preparative TLC plate (20 x 20 cm, 500 mum) using 8:2 EtOAc/hexane as eluant to provide [1-benzyl-3-({3-[(2,2-dimethyl-propylamino)-methylene]-2-oxo- 2,3-dihydro- 1H-indole-5-sulfonyl}-isobutyl-amino)-2-hydroxy-propyl]-carbamic acid hexahydro- furo[2,3-b]furan-3-yl ester 9n (24 mg, 70%). MS m/z 685.3 (MH)+, 1H NMR (CDCl3) 9.15 (m, 1H), 8.70 (s, 1H), 7.66 (s, 1H), 7.61 (d, J = 13.2, 1H),7.43 (dd, J = 8.4, 2.0, 1H), 7.24 (m, 5H), 7.00 (d, J = 8.0, 1H), 5.64 (d, J = 5.2, 1H), 5.11 (d, J = 8.4, 1H), 5.00 (m, 1H), 3.65 - 3.93 (m, 7H), 3.18 (d, J = 6.8, 2H), 2.75 - 3.22 (m, 7H), 1.83 (m, 1H), 1.60 (m, 1H), 1.42 (m, 1H), 1.01 (s, 9H), 0.84 - 0.95 (m, 6H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | With sodium hydroxide; In water;pH 10.0; | Quinolin-2-ylmethanamine bischlorohydrate 15 (0.5 g, 2.1 mmol) was neutralized drop by drop with sodium hydroxide (1M, 30 mL) up to pH=10. The aqueous phase was extracted by CH2Cl2 (4×25 mL), then dried over magnesium sulfate, filtered, and evaporated to dryness affording the free amine 12. 82% yield; 1H NMR (300 MHz, CDCl3) delta 1.94 (2H, s, NH2), 4.16 (2H, s, CH2), 7.42 (1H, m, CHar), 7.49 (1H, m, CHar), 7.54 (1H, m, CHar), 7.68 (1H, m, CHar), 7.80 (1H, m, CHar), 8.06 (2H, m, CHar); 13C NMR (75 MHz, CDCl3) 30.72, 117.69, 123.87, 128.59, 129.08, 129.64, 131.54, 132.94, 138.50, 147.43. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Example 65 (3S)-2-(2R)-3-Cyclopentyl-2-[formyl(hydroxy)amino]methyl}propanoyl)-N-(2-quinolinylmethyl)-3-pyrazolidinecarboxamide (2-quinolinylmethyl)amine (80 mg, 0.409 mmol). MS (ES+) m/z 453.8 (MH+). | ||
| Example 65 (3S)-2-((2R)-3-Cyclopentyl-2-[formyl(hydroxy)amino]methyl}propanoyl)-N-(2-quinolinylmethyl)-3-pyrazolidinecarboxamide (2-quinolinylmethyl)amine (80 mg, 0.409 mmol). MS (ES+) m/z 453.8 (MH+). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In cyclohexanone; at 130℃; for 1h; | The catalyst precursor, preferably [RuCI2(COD)]m (1 eq.), 1 ,4-bis(diphenylphosphino)butane (1 .0-1 .2 eq., preferably 1 .0 eq.) and 2- quinolinylmethylamine (1.0-1 .4 eq., preferably 1.225 eq.) were dissolved in one of the above mentioned solvents, preferably cyclohexanone (10- 20 ml/g Ru-precursor, preferably 20 ml/g). The mixture was heated at 130 C for 1 hour and then cooled to ambient temperature. The solid precipitate was filtered off and washed with the same solvent that was used for the reaction. A person skilled in the art can determine the cis-/trans- isomeric ratio by NMR. The diastereomeric ratios generated by this method are usually in the range of d.r. (diastereomeric ratio) >98% towards the cis isomer. The same results can be achieved starting with [RuCI2(dmso-KS)3(dmso-KO)], [RuCI2(dmso-KS)4]or [RuCI2(bicyclo[2.2.1]hepta-2,5-diene)]m as precursor |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen; In tetrahydrofuran; methanol; at 50℃; under 3102.97 Torr; for 12h; | General procedure: To a mixture of oxime (0.86mmol) and Raney Co 2724 (200 mg, slurry in H2O) were addedTHF (1.5 mL) and MeOH (1.5 mL). The reaction mixture waspurged with nitrogen twice then pressurized to 60 psi H2 at 50C. The reaction was deemed complete when H2 consumptionceased, typically after 2-10 h. Upon completion, the reactionwas filtered through a pad of celite and washed with MeOH. Thefiltrate was then concentrated under reduced pressure, andpurified by flash chromatography (CH2Cl2-MeOH, 95:5) tofurnish the title compound. Alternatively, the product was convenientlyisolated in high purity as the HCl salt. After filteringoff the catalyst, the filtrate solvent was changed to MTBE (1.5mL) and HCl (0.95 mmol, 1 M in Et2O) was added dropwise tocrystallize the salt. The resulting HCl amine salt was then isolatedby filtration and washed with MTBE. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triphenylphosphine; In tetrahydrofuran; water; at 20℃; for 5h; | General procedure: NaN3 (0.65 g, 10 mmol) was added carefully to a solution of 5a(1.78 g, 5 mmol) in DMF (10 mL). The reaction was stirred overnightat room temperature. The reaction mixture was extractedwith EtOAc/H2O. Then the organic layer was washed with brine,dried over anhydrous MgSO4, and the solution was evaporatedunder vacuum to give the crude product 2-(azidomethyl)-N-benzylquinoline-4-carboxamide.PPh3 (1.57 g, 6 mmol) was added to a solution of 2-(azidomethyl)-N-benzylquinoline-4-carboxamide in TFH/H2O (20 mL,9:1). Five hours later, the solution was concentrated under vacuumand the residue was added to 1 M HCl (20 mL). The mixture wasstirred for 30 min, then the mixture was filtered to get aqueousphase. The aqueous phase was basified to pH 10 by the NaHCO3,and extracted with CH2Cl2 (3 50 mL). The combined organiclayer was washed with brine, dried over anhydrous MgSO4, andthe solution was evaporated under vacuum to give target compound6a without purification for next procedure.Compounds 6b-6k were synthesized by the same methoddescribed above. |
[ 5760-20-3 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 31% | With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃; for 16h;Reflux; | General procedure: To a solution of 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine (1 equiv) and diisopropylethylamine (1.5 equiv) in 2-propanol was added amine (1.2 equiv). After refluxing for 16 h, the reaction mixture was concentrated in vacuo and the appropriate solvent added to precipitate the crude product, which was collected by filtration and then purified by recrystallization, prep HPLC or column chromatography. |
[ 5760-20-3 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 16h; | Step 1: (S) -tert-Butyl (1- (2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) -4- ( (quinolin-2-ylmethyl) carbamoyl) oxazol-5-yl) ethyl) carbamate[1470]To 15 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazole-4-carboxylic acid (0.3 g, 0.64 mmol) , <strong>[5760-20-3]quinolin-2-ylmethanamine</strong> (121 mg, 0.77 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (184 mg, 0.96 mmol) and 1-hydroxy-7-azabenzotriazole (217 mg, 1.60 mmol) . To the mixture was added N, N-diisopropylethylamine (0.45 mL, 2.56 mmol) dropwise at 0 . The mixture was stirred at rt for 16 hours. The solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 3/1) to give a white solid (366 mg, 94) .[1471]1H NMR (600 MHz, CDCl3) : delta ppm 8.20 (d, J 8.4 Hz, 1H) , 8.13 (d, J 8.5 Hz, 1H) , 7.86 (d, J 8.0 Hz, 1H) , 7.79 -7.76 (m, 1H) , 7.66 -7.65 (m, 2H) , 7.59 (t, J 7.4 Hz, 1H) , 7.48 (d, J 8.4 Hz, 1H) , 7.28 (d, J 8.6 Hz, 2H) , 7.12 -7.11 (m, 1H) , 6.74 (t, JF-H 75.0 Hz, 1H) , 5.34 -5.30 (m, 1H) , 4.98 -4.97 (m, 2H) , 4.03 (d, J 7.0 Hz, 2H) , 1.58 (d, J 7.0 Hz, 3H) , 1.46 (s, 9H) , 1.41 -1.37 (m, 1H) , 0.74 -0.71 (m, 2H) , 0.46 -0.44 (m, 2H) and MS-ESI: m/z 609.3 [M+H]+. |
[ 5760-20-3 ]
[ 2168-78-7 ]
[ 1576-35-8 ]
[ 5760-20-3 ]
[ 2168-78-7 ]
[ 1950-68-1 ]

A650215 [18004-62-1]
Quinolin-2-ylmethanamine dihydrochloride
Reason: Free-salt