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[ CAS No. 81748-72-3 ]

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Chemical Structure| 81748-72-3
Chemical Structure| 81748-72-3
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Product Details of [ 81748-72-3 ]

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 :

Safety of [ 81748-72-3 ]

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:

Application In Synthesis of [ 81748-72-3 ]

* 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.

  • Downstream synthetic route of [ 81748-72-3 ]

[ 81748-72-3 ] Synthesis Path-Downstream   1~30

  • 1
  • <i>N</i>-(8-hydroxy-[5]quinolylmethyl)-benzamide [ No CAS ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
YieldReaction ConditionsOperation in experiment
8-Hydroxy-5-acetaminomethyl-chinolin, HCl, Hydrolyse (als Dihydrochlorid);
  • 3
  • [ 148-24-3 ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation 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
  • 4
  • [ 81748-72-3 ]
  • [ 777085-55-9 ]
  • C20H24N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃;
  • 5
  • [ 81748-72-3 ]
  • [ 1094606-91-3 ]
  • [ 1094606-82-2 ]
YieldReaction ConditionsOperation in experiment
49% With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide
  • 6
  • [ 81748-72-3 ]
  • Fmoc-Glu(O-t-Bu)-NHS [ No CAS ]
  • C34H35N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
  • 7
  • C40H36BN8O4(1-)*Li(1+) [ No CAS ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation in experiment
With water In methanol
  • 8
  • [ 10136-57-9 ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 81748-72-3 ]
  • [ 1078-61-1 ]
  • [ 1094606-80-0 ]
YieldReaction ConditionsOperation 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
  • 10
  • [ 81748-72-3 ]
  • [ 28920-43-6 ]
  • (9H-fluoren-9-yl)methyl (8-hydroxyquinolin-5-yl)methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With sodium hydrogencarbonate In water; N,N-dimethyl-formamide
  • 11
  • [ 81748-72-3 ]
  • [ 59-30-3 ]
  • C29H27N9O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With HBTU; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide
  • 12
  • [ 81748-72-3 ]
  • [ 84889-09-8 ]
  • C43H38N4O5 [ No CAS ]
  • 13
  • [ 81748-72-3 ]
  • [ 760190-09-8 ]
  • [ 1094606-83-3 ]
YieldReaction ConditionsOperation in experiment
98.6 mg With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
  • 17
  • [ 81748-72-3 ]
  • [ 292638-85-8 ]
  • [ 1283093-93-5 ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; for 24h;
  • 18
  • 2-((8-hydroxyquinolin-5-yl)methyl)isoindoline-1,3-dione [ No CAS ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation 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%.
  • 19
  • [ 81748-72-3 ]
  • [ 3140-75-8 ]
  • C54H39N9O6 [ No CAS ]
  • 20
  • [ 81748-72-3 ]
  • [ 951-82-6 ]
  • C21H22N2O5 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 21
  • [ 81748-72-3 ]
  • [ 104-03-0 ]
  • C18H15N3O4 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 22
  • [ 81748-72-3 ]
  • [ 405-50-5 ]
  • C18H15FN2O2 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 23
  • [ 81748-72-3 ]
  • [ 32857-62-8 ]
  • C19H15F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 24
  • [ 4053-45-6 ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation 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
  • 25
  • [ 1005143-73-6 ]
  • [ 81748-72-3 ]
YieldReaction ConditionsOperation 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;
  • 26
  • [ 81748-72-3 ]
  • N-((8-hydroxy-7-(pyrrolidin-1-ylmethyl)quinolin-5-yl)methyl)-2-(3,4,5-trimethoxyphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 27
  • [ 81748-72-3 ]
  • N-((8-hydroxy-7-(pyrrolidin-1-ylmethyl)quinolin-5-yl)methyl)-2-(4-nitrophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 28
  • [ 81748-72-3 ]
  • 2-(4-fluorophenyl)-N-((8-hydroxy-7-(pyrrolidin-1-ylmethyl)quinolin-5-yl)methyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 29
  • [ 81748-72-3 ]
  • 1-(4-bromobenzyl)-3-((8-hydroxy-7-(pyrrolidin-1-ylmethyl)quinolin-5-yl)methyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere 2: ethanol / Reflux; Inert atmosphere
  • 30
  • [ 81748-72-3 ]
  • 1-bromo-4-(isocyanatomethyl)benzene [ No CAS ]
  • 1-(4-bromobenzyl)-3-((8-hydroxyquinolin-5-yl)methyl)urea [ No CAS ]
YieldReaction ConditionsOperation 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.
Historical Records

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