Alternatived Products of [ 727650-61-5 ]
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 : |
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Safety of [ 727650-61-5 ]
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 ]
- 1
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[ 24306-33-0 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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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 |
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- 2
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[ 1022151-47-8 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 3
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[ 13669-57-3 ]

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[ 727650-61-5 ]
- 4
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[ 1337882-50-4 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation 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
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[ 1427474-53-0 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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
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[ 727650-61-5 ]

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[ 1427474-56-3 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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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 |
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- 7
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[ 727650-61-5 ]

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[ 1427474-70-1 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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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 |
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- 8
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[ 24424-99-5 ]

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[ 727650-61-5 ]

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[ 1427474-54-1 ]
Yield | Reaction Conditions | Operation 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
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[ 580-16-5 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 10
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[ 727650-61-5 ]

-
[ 23095-05-8 ]

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[ 1451273-43-0 ]
Yield | Reaction Conditions | Operation 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
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[ 104-94-9 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 12
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[ 159454-73-6 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 13
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[ 29507-86-6 ]

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[ 727650-61-5 ]
Yield | Reaction Conditions | Operation 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
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[ 727650-61-5 ]

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[ 1451274-40-0 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: pyridine / 12 h / 40 °C
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere |
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- 15
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[ 727650-61-5 ]

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[ 1451273-46-3 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 16
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[ 727650-61-5 ]

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[ 1451273-47-4 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 17
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[ 727650-61-5 ]

-
[ 1451273-48-5 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 18
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[ 727650-61-5 ]

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[ 1451273-49-6 ]
Yield | Reaction Conditions | Operation in experiment |
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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 |
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- 19
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[ 7101-95-3 ]

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[ 727650-61-5 ]
- 20
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[ 7101-96-4 ]

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[ 727650-61-5 ]