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CAS No. : | 81748-72-3 | MDL No. : | MFCD06740638 |
Formula : | C10H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 174.20 g/mol | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
GHS Pictogram: |
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* 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 hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8-Hydroxy-5-acetaminomethyl-chinolin, HCl, Hydrolyse (als Dihydrochlorid); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2SO4 2: concentrated aqueous HCl | ||
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 12 h / 20 °C 2: N,N-dimethyl-formamide / 5 h / 150 °C 3: hydrogenchloride / water / 20 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 5-(chloromethyl)quinolin-8-ol With hexamethylenetetramine In dimethyl sulfoxide at 20℃; Stage #2: With hydrogenchloride In water at 20℃; for 48h; | |
Stage #1: 5-(chloromethyl)quinolin-8-ol With potassium phtalimide In N,N-dimethyl-formamide at 150℃; for 5h; Stage #2: With hydrogenchloride In water at 150℃; for 9h; | ||
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 5 h / 150 °C 2: hydrogenchloride / water / 20 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Stage #1: 5-(aminomethyl)-8-hydroxyquinoline; dihydrocaffeic acid With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide Stage #2: With trifluoroacetic acid In dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium hydrogencarbonate In water; N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.6 mg | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate In acetonitrile at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In acetonitrile at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In acetonitrile at 50℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogenchloride In water at 20℃; Reflux; | |
75% | With hydrogenchloride for 12h; Reflux; | 5 Example 5 5-(Aminomethyl)quinoline-8-ol Add 2-(((8-hydroxyquinolin-5-yl)methyl)isoindolin-1,3-dione (780 mg, 2.56 mmol) to concentrated hydrochloric acid (50 mL). Heat to reflux After 12 hours, the solution changed from turbid to clear, and the reaction was completed.After cooling to room temperature, the solid obtained after vacuum drying was dissolved in water, sodium bicarbonate solution was added to adjust the pH to neutral, and then suction filtered to obtain 334.47 mg of brown solid with a yield of 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | General procedure for synthesis of 5a-5f General procedure: To a stirred solution of compound 4 (1.0mmol, 140mg) or 5-amino-8-hydroxyquinoline dihydrochloride and carboxylic acid (1.2mmol) in DMF-H2O (1:5) were added oxyma (2.0mmol, 284mg), EDCI (2.0mmol, 310mg), and NaHCO3 (6.0mmol, 636mg). After stirring at room temperature for 12h, the solution was extracted with EtOAc. The combined organic layers were washed with brine (3mL), and then dried over Na2SO4. Concentration of organic phase gave crude product which was directly used for next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide Inert atmosphere; | General procedure for synthesis of 5a-5f General procedure: To a stirred solution of compound 4 (1.0mmol, 140mg) or 5-amino-8-hydroxyquinoline dihydrochloride and carboxylic acid (1.2mmol) in DMF-H2O (1:5) were added oxyma (2.0mmol, 284mg), EDCI (2.0mmol, 310mg), and NaHCO3 (6.0mmol, 636mg). After stirring at room temperature for 12h, the solution was extracted with EtOAc. The combined organic layers were washed with brine (3mL), and then dried over Na2SO4. Concentration of organic phase gave crude product which was directly used for next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide Inert atmosphere; | General procedure for synthesis of 5a-5f General procedure: To a stirred solution of compound 4 (1.0mmol, 140mg) or 5-amino-8-hydroxyquinoline dihydrochloride and carboxylic acid (1.2mmol) in DMF-H2O (1:5) were added oxyma (2.0mmol, 284mg), EDCI (2.0mmol, 310mg), and NaHCO3 (6.0mmol, 636mg). After stirring at room temperature for 12h, the solution was extracted with EtOAc. The combined organic layers were washed with brine (3mL), and then dried over Na2SO4. Concentration of organic phase gave crude product which was directly used for next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide Inert atmosphere; | General procedure for synthesis of 5a-5f General procedure: To a stirred solution of compound 4 (1.0mmol, 140mg) or 5-amino-8-hydroxyquinoline dihydrochloride and carboxylic acid (1.2mmol) in DMF-H2O (1:5) were added oxyma (2.0mmol, 284mg), EDCI (2.0mmol, 310mg), and NaHCO3 (6.0mmol, 636mg). After stirring at room temperature for 12h, the solution was extracted with EtOAc. The combined organic layers were washed with brine (3mL), and then dried over Na2SO4. Concentration of organic phase gave crude product which was directly used for next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium azide / acetone / 20 h / Reflux; Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With palladium 10% on activated carbon; hydrogen In ethyl acetate Reflux; | 38 Synthesis of 91 5-(aminomethyl)quinolin-8-ol (4) A suspension of azide 88 3 (2.00g, 10mol) and 10% 92 Pd/C (0.15g) in 93 ethylacetate (15mL) was hydrogenated overnight, the reaction mixture was filtered off and washed with dichloromethane-methanol (1:1). The combined filtration was evaporated under vacuum to give the oily crude which was purified with flash chromatography on silica. Compound 4 was eluted out with dichloromethane/94 methanol (15:0-10:1) (1.18g, 68%). 1H NMR (400MHz, DMSO-d6) δ 8.86 (dd, J=4.1, 1.6Hz, 1H), 8.57 (dd, J=8.6, 1.6Hz, 1H), 7.58 (dd, J=8.5, 4.1Hz, 1H), 7.44 (dd, J=7.8, 0.9Hz, 1H), 7.02 (d, J=7.8Hz, 1H), 4.10 (d, J=0.8Hz, 2H). |
With water; triphenylphosphine In tetrahydrofuran at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydrogencarbonate; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide; water / 12 h / 20 °C / Inert atmosphere 2: ethanol / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydrogencarbonate; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide; water / Inert atmosphere 2: ethanol / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydrogencarbonate; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide; water / Inert atmosphere 2: ethanol / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere 2: ethanol / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trimethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere; | 39 Synthesis of 1-(4-bromobenzyl)-3-((8-hydroxyquinolin-5-yl)methyl)urea (7) To a stirred solution of compound 91 4 (1.0mmol, 140mg) and 96 4-bromobenzyl isocyanate (1.0mmol, 212mg) in anhydrous 97 dichloromethane (5mL) were added catalytic amount of 98 trimethylamine (0.1mmol, 10.1mg). After stirring at room temperature for 5h, solvent was removed under reduced pressure to give crude 99 product which was directly used for next step without purification. |
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