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[ CAS No. 727650-61-5 ]

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Chemical Structure| 727650-61-5
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Product Details of [ 727650-61-5 ]

CAS No. :727650-61-5 MDL No. :MFCD18413388
Formula : C9H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :LDCBQRZNYYAODD-UHFFFAOYSA-N
M.W :160.17 Pubchem ID :22326815
Synonyms :

Safety of [ 727650-61-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 727650-61-5 ]

* 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 [ 727650-61-5 ]

[ 727650-61-5 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 24306-33-0 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: bromine; pyridine / tetrachloromethane / 3 h / 0 - 90 °C 2: potassium carbonate; water / methanol / 2 h / 20 °C 3: potassium carbonate / acetone / 20 °C 4: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
Multi-step reaction with 5 steps 1: pyridine; bromine / tetrachloromethane / 3 h / 0 - 90 °C 2: potassium carbonate; water / methanol / 1 h / 20 °C 3: potassium carbonate / acetone / 20 °C 4: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / toluene / 8 h / 100 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
  • 2
  • [ 1022151-47-8 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; water / methanol / 2 h / 20 °C 2: potassium carbonate / acetone / 20 °C 3: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
Multi-step reaction with 4 steps 1: potassium carbonate; water / methanol / 1 h / 20 °C 2: potassium carbonate / acetone / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / toluene / 8 h / 100 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
  • 4
  • [ 1337882-50-4 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / toluene / 8 h / 100 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
  • 5
  • [ 1427474-53-0 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; for 8h; 3-aminoquinolin-6-ol (Q29.ii) 3-aminoquinolin-6-ol (Q29.ii) was obtained by adding to a solution of Q29.i (1.0 g, 2.94 mmol) in MeOH (10 ml), 10% Palladium on carbon (0.313 g, 0.294 mmol), and stirring the reaction mixture under H2 atmosphere (1 atm) at 60°C for 8 h. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to afford the title compound as pale yellow solid (0.5 g, 80% yield). The crude product was used without further purification. LCMS (method B): [M+H]+ = 161 , tR = 0.31 min.
0.5 g With palladium 10% on activated carbon; hydrogen In methanol at 60℃; for 8h; 3-aminoquinolin-6-ol (Q29.ii) was obtained by adding to a solution of Q29.i (1.0 g, 2.94 mmol) in MeOH (10 ml), 10% Palladium on carbon (0.313 g, 0.294 mmol), and stirring the reaction mixture under H2 atmosphere (1 atm) at 60° C. for 8 h. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to afford the title compound as pale yellow solid (0.5 g, 80% yield). The crude product was used without further purification. LCMS (method B): [M+H]+=161, tR=0.31 min
  • 6
  • [ 727650-61-5 ]
  • [ 1427474-56-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 24 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C 2.2: 3 h / 20 °C
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 24 h / Reflux 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 2.2: 3 h / 20 °C
  • 7
  • [ 727650-61-5 ]
  • [ 1427474-70-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 24 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C 2.2: 3 h / 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.16 h / 110 °C / Inert atmosphere; Microwave irradiation
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 24 h / Reflux 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 2.2: 3 h / 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 110 °C / Inert atmosphere; Microwave irradiation
  • 8
  • [ 24424-99-5 ]
  • [ 727650-61-5 ]
  • [ 1427474-54-1 ]
YieldReaction ConditionsOperation in experiment
0.5 g In tetrahydrofuran for 24h; Reflux; tert-butyl 6-hydroxyquinolin-3-ylcarbamate (Q29.iii) To a solution of Q29.N (0.5 g, 3.12 mmol) in THF (10 ml), (Boc)20 (1 .450 ml, 6.24 mmol) was added, and the reaction mixture was stirred at reflux for 24 h. THF was removed under reduced pressure. The residue was dissolved in EtOAc (50 ml), subsequently washed with 1 % HCI solution (10 ml), water (10 ml), sat. 60% NaHCO3 (10 ml) and brine (10 ml). The organic phase was dried over MgS04, filtered and concentrated to afford the crude product as brown oil, which was purified by silica gel chromatography (DCM/MeOH = 30/1 ) to afford the title compound as white solid (0.5 g, 61 .5% yield). LCMS(method B): [M+H]+ = 261 , tR = 2.17 min.
0.5 g In tetrahydrofuran for 24h; Reflux; tert-butyl 6-hydroxyquinolin-3-ylcarbamate (Q29.iii) To a solution of Q29.ii (0.5 g, 3.12 mmol) in THF (10 ml), (Boc)2O (1.450 ml, 6.24 mmol) was added, and the reaction mixture was stirred at reflux for 24 h. THF was removed under reduced pressure. The residue was dissolved in EtOAc (50 ml), subsequently washed with 1% HCl solution (10 ml), water (10 ml), sat. 60% NaHCO3 (10 ml) and brine (10 ml). The organic phase was dried over MgSO4, filtered and concentrated to afford the crude product as brown oil, which was purified by silica gel chromatography (DCM/MeOH=30/1) to afford the title compound as white solid (0.5 g, 61.5% yield). LCMS (method B): [M+H]+=261, tR=2.17 min.
  • 9
  • [ 580-16-5 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridine / dichloromethane / 8 h / 0 - 20 °C 2: bromine; pyridine / tetrachloromethane / 3 h / 0 - 90 °C 3: potassium carbonate; water / methanol / 2 h / 20 °C 4: potassium carbonate / acetone / 20 °C 5: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / Inert atmosphere 6: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
Multi-step reaction with 6 steps 1: pyridine / dichloromethane / 8 h / 0 - 20 °C 2: pyridine; bromine / tetrachloromethane / 3 h / 0 - 90 °C 3: potassium carbonate; water / methanol / 1 h / 20 °C 4: potassium carbonate / acetone / 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / toluene / 8 h / 100 °C / Inert atmosphere 6: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
  • 10
  • [ 727650-61-5 ]
  • [ 23095-05-8 ]
  • [ 1451273-43-0 ]
YieldReaction ConditionsOperation in experiment
25% With pyridine at 40℃; for 12h; IX-1.5 5-Bromo-N-(6-hydroxyquinolin-3-yl)-2-methoxybenzenesulfonamide A solution of 3-aminoquinolin-6-ol (150 mg, 0.9 mmol) and 5-bromo-2- methoxybenzene-l-sulfonyl chloride (143 mg, 0.5 mmol) in pyridine (5 mL) was heated to 40 °C for 12 h. The reaction mixture was concentrated in vacuum and the residue was purified by silica gel column (PE/EtOAc, 10/1) to give 50 mg (yield: 25%) of 5-bromo-N-(6- hydroxyquinolin-3-yl)-2-methoxybenzenesulfonamide as white solid. [00674] 1H NMR (DMSO-d6, 400MHz): δ = 10.59 (1H, brs), 10.06 (1H, brs), 8.42 (1H, s), 7.85 (1H, s), 7.78-7.73 (3H, m), 7.20-7.17 (2H, m), 7.03 (1H, s), 3.85 (3H, s). MS: m/z 409.2 (M+H+).
  • 11
  • [ 104-94-9 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water / 0.17 h 1.2: 0.33 h / Inert atmosphere; Reflux 1.3: 50 h / Reflux; Inert atmosphere 2.1: hydrogenchloride; tin(II) chloride hydrate / 0.22 h / 50 °C 3.1: boron tribromide / dichloromethane / 12 h / -60 °C
  • 12
  • [ 159454-73-6 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; tin(II) chloride hydrate / 0.22 h / 50 °C 2: boron tribromide / dichloromethane / 12 h / -60 °C
  • 13
  • [ 29507-86-6 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
55% With boron tribromide In dichloromethane at -60℃; for 12h; IX-1.4 To a vigorously suspension of 6-methoxyquinolin-3 -amine (1.0 g, 5.7 mol) in anhydrous CH2C12 (20 mL) at -60 °C was added BBr3 (3.0 mL) portionwise over 20 minutes. The mixture was stirred vigorously for an additional 12 h and diluted with water to 100 mL. The aqueous layer was extracted with EtOAc (25 mL x3). The extracts were washed brine and dried over Na2S04. The mixture was concentrated to dryness and the residue was purified by silica gel column (DCM/MeOH, 10/1) to give 500 mg (yield: 55%) of 3-aminoquinolin-6-ol as brown solid. MS: m/z 161.1 (M+H+).
  • 14
  • [ 727650-61-5 ]
  • [ 1451274-40-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 40 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 15
  • [ 727650-61-5 ]
  • [ 1451273-46-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 12 h / 40 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 17 h / 90 °C / 2585.81 Torr
  • 16
  • [ 727650-61-5 ]
  • [ 1451273-47-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / 12 h / 40 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 17 h / 90 °C / 2585.81 Torr 4: lithium hydroxide; water / tetrahydrofuran / 0 - 20 °C
  • 17
  • [ 727650-61-5 ]
  • [ 1451273-48-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / 12 h / 40 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 17 h / 90 °C / 2585.81 Torr 4: ammonia / water / 2 h / 80 °C
  • 18
  • [ 727650-61-5 ]
  • [ 1451273-49-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / 12 h / 40 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 17 h / 90 °C / 2585.81 Torr 4: methanol / 2 h / 80 °C
  • 19
  • [ 7101-95-3 ]
  • [ 727650-61-5 ]
  • 20
  • [ 7101-96-4 ]
  • [ 727650-61-5 ]
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