4-hydroxy-6-methoxy-7-benzyloxyquinoline
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Stage #1: 7-benzyloxy-4-hydroxy-6-methoxyquinoline With trichlorophosphate for 2h; Heating / reflux; Stage #2: With sodium hydrogencarbonate; sodium carbonate In water at 20℃; pH=8; | 95% |
With trichlorophosphate for 2h; Heating / reflux; | 95% |
With trichlorophosphate In toluene at 120℃; for 1.5h; | 90% |
4-chloro-6-methoxy-7-hydroxyquinoline
benzyl bromide
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 2h; | 95% |
6-methoxy-7-benzyloxy-4(1H)-quinolinone
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Stage #1: 6-methoxy-7-benzyloxy-4(1H)-quinolinone With trichlorophosphate at 110℃; for 3h; Stage #2: With sodium carbonate In chloroform; water Cooling with ice; | 94% |
With sodium hydroxide; trichlorophosphate In chloroform | 21% |
With trichlorophosphate In acetonitrile for 6h; Reflux; | 174.8 g |
1-(2-amino-4-(benzyloxy)-5-methoxyphenyl)ethanone
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 1.2: 8 h 2.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 1.2: Inert atmosphere 2.1: trichlorophosphate / 10 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h 1.2: 15 h / 20 °C 2.1: trichlorophosphate / 4.33 h / Cooling with ice; Reflux View Scheme |
benzyl bromide
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 1 h / 0 °C / pH 7 - 8 3.1: ammonium formate; iron / toluene; water / 103 °C 4.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 4.2: 8 h 5.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 2.25 h / 0 °C 3.1: iron; ammonium acetate / toluene; water / 105 °C 4.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 4.2: Inert atmosphere 5.1: trichlorophosphate / 10 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: nitric acid / dichloromethane / 2 h / -20 - -10 °C 3.1: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 4.1: iron; acetic acid / 2 h / 60 - 90 °C 5.1: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme |
4-benzyloxy-3-methoxyacetophenone
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: nitric acid; sulfuric acid / dichloromethane / 1 h / 0 °C / pH 7 - 8 2.1: ammonium formate; iron / toluene; water / 103 °C 3.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 3.2: 8 h 4.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: nitric acid; sulfuric acid / dichloromethane / 2.25 h / 0 °C 2.1: iron; ammonium acetate / toluene; water / 105 °C 3.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 3.2: Inert atmosphere 4.1: trichlorophosphate / 10 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1: nitric acid / dichloromethane / 2 h / -20 - -10 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 3: iron; acetic acid / 2 h / 60 - 90 °C 4: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme |
1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)ethanone
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonium formate; iron / toluene; water / 103 °C 2.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 2.2: 8 h 3.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: iron; ammonium acetate / toluene; water / 105 °C 2.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 2.2: Inert atmosphere 3.1: trichlorophosphate / 10 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 2: iron; acetic acid / 2 h / 60 - 90 °C 3: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme |
1-(3-methoxy-4-hydroxyphenyl)ethanone
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 1 h / 0 °C / pH 7 - 8 3.1: ammonium formate; iron / toluene; water / 103 °C 4.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 4.2: 8 h 5.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 2.25 h / 0 °C 3.1: iron; ammonium acetate / toluene; water / 105 °C 4.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 4.2: Inert atmosphere 5.1: trichlorophosphate / 10 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: nitric acid / dichloromethane / 2 h / -20 - -10 °C 3.1: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 4.1: iron; acetic acid / 2 h / 60 - 90 °C 5.1: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme |
5-{[(3-(benzyloxy)-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6- dione
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: biphenyl / diphenylether / 1 h / 220 °C / Inert atmosphere 2: trichlorophosphate / 5 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 2 steps 1: 1,2-dichloro-benzene / 7 h / 180 °C 2: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1,2-dichloro-benzene / 7 h / 180 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: iron; acetic acid / 2 h / 60 - 90 °C 2: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme |
2-(benzyloxy)-1-methoxy-4-nitrobenzene
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ammonium chloride; iron / ethanol; water / 1 h / 20 °C / Reflux 2: ethanol / 1 h / Reflux 3: 1,2-dichloro-benzene / 7 h / 180 °C 4: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme | |
Multi-step reaction with 4 steps 1: iron / ethanol; water / Reflux 2: ethanol / 1 h / 80 °C 3: 1,2-dichloro-benzene / 7 h / 180 °C 4: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme |
3-benzyloxy-4-methoxybenzeneamine
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ethanol / 1 h / Reflux 2: 1,2-dichloro-benzene / 7 h / 180 °C 3: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme | |
Multi-step reaction with 3 steps 1: ethanol / 1 h / 80 °C 2: 1,2-dichloro-benzene / 7 h / 180 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme |
5-nitroguaiacol
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2: ammonium chloride; iron / ethanol; water / 1 h / 20 °C / Reflux 3: ethanol / 1 h / Reflux 4: 1,2-dichloro-benzene / 7 h / 180 °C 5: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C 2: iron / ethanol; water / Reflux 3: ethanol / 1 h / 80 °C 4: 1,2-dichloro-benzene / 7 h / 180 °C 5: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-chloro-6-methoxy-7-hydroxyquinoline
Conditions | Yield |
---|---|
With methanesulfonic acid; trifluoroacetic acid for 3h; Reflux; Inert atmosphere; | 100% |
Stage #1: 7-(benzyloxy)-4-chloro-6-methoxyquinoline With methanesulfonic acid; trifluoroacetic acid for 3h; Reflux; Stage #2: With sodium hydroxide for 2h; pH=7; | 100% |
With trifluoroacetic acid at 75℃; for 6h; | 95.4% |
With hydrogen bromide; acetic acid In water at 80℃; for 3h; | 80% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-Amino-3-chlorophenol hydrochloride
4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chloroaniline
Conditions | Yield |
---|---|
With sodium hydride; potassium carbonate In N,N-dimethyl-formamide; mineral oil at 100℃; for 2h; Inert atmosphere; | 98% |
With dimethyl sulfoxide In methanol; water | 66% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-(7-benzyloxy-6-methoxyquinolin-4-yloxy)aniline
Conditions | Yield |
---|---|
Stage #1: 4-amino-phenol With sodium methylate In methanol; ISOPROPYLAMIDE at 20℃; for 1h; Stage #2: 7-(benzyloxy)-4-chloro-6-methoxyquinoline In ISOPROPYLAMIDE at 120℃; for 22h; | 96% |
Multi-step reaction with 2 steps 1.1: 1-methyl-pyrrolidin-2-one / 2 h / 150 °C 2.1: hydrogenchloride; methanol; water / 6 h / Heating / reflux 2.2: pH 12 View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 140 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol; water / 2 h / 90 °C / Inert atmosphere View Scheme |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
2-fluoro-4-nitrophenol
7-benzyloxy-4-(2-fluoro-4-nitro-phenoxy)-6-methyloxyquinoline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In chlorobenzene at 140℃; for 18h; | 92% |
With N-ethyl-N,N-diisopropylamine In chlorobenzene for 48h; Reflux; | 82% |
With N-ethyl-N,N-diisopropylamine In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; | 81% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
Conditions | Yield |
---|---|
With dmap at 160℃; for 4h; | 90.5% |
4-nitro-phenol
7-(benzyloxy)-4-chloro-6-methoxyquinoline
7-(benzyloxy)-6-methoxy-4-(4-nitrophenoxy)quinoline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In xylene for 12h; Reflux; | 84.3% |
In chlorobenzene for 16h; Reflux; | 62.4% |
In chlorobenzene for 20h; Reflux; | 201.8 g |
1-(2-fluoro-3-hydroxy-6-nitrophenyl)propan-2-one
7-(benzyloxy)-4-chloro-6-methoxyquinoline
1-(3-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-2-fluoro-6-nitrophenyl)propan-2-one
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 100℃; | 84% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
3-fluoro-4-nitrophenol
7-(benzyloxy)-4-(3-fluoro-4-nitrophenoxy)-6-methoxyquinoline
Conditions | Yield |
---|---|
In chlorobenzene at 120℃; for 21h; | 82% |
Stage #1: 7-(benzyloxy)-4-chloro-6-methoxyquinoline; 3-fluoro-4-nitrophenol In chlorobenzene at 120℃; for 21h; Stage #2: With sodium hydroxide In chloroform; water; chlorobenzene at 20℃; | 82% |
With N-ethyl-N,N-diisopropylamine In chlorobenzene at 140℃; for 15h; | 50% |
With sodium hydroxide In chloroform; chlorobenzene | 47% |
In chlorobenzene for 16h; Reflux; |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
methyl-phenyl-thioether
4-chloro-6-methoxy-7-hydroxyquinoline
Conditions | Yield |
---|---|
With sodium hydroxide; methanesulfonic acid In hexane; trifluorormethanesulfonic acid | 75% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-amino-2-fluorophenol
4-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorobenzenamine
Conditions | Yield |
---|---|
Stage #1: 4-amino-2-fluorophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 7-(benzyloxy)-4-chloro-6-methoxyquinoline In N,N-dimethyl-formamide; mineral oil at 100℃; for 30h; | 73% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
N-(3-fluoro-4-hydroxyphenyl)-N'-(2-phenylethyl)ethanediamide
Conditions | Yield |
---|---|
With dmap; bromobenzene for 6h; Heating / reflux; | 61% |
With dmap In bromobenzene for 6h; Heating / reflux; | 61% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
para-nitrobenzenethiol
Conditions | Yield |
---|---|
In chlorobenzene for 16h; Reflux; | 60.1% |
6-hydroxy-N-methyl-1-naphthalenecarboxamide
7-(benzyloxy)-4-chloro-6-methoxyquinoline
6-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 120℃; for 24h; Reagent/catalyst; Solvent; Temperature; Time; Concentration; | 58% |
With dmap In 1,4-dioxane for 72h; Product distribution / selectivity; Heating / reflux; |
Conditions | Yield |
---|---|
In chlorobenzene for 16h; Reflux; | 52.4% |
In chlorobenzene for 18h; Reflux; |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
2,5-dimethyl-4-amino phenol
4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylaniline
Conditions | Yield |
---|---|
With dimethyl sulfoxide In methanol; water | 52% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-amino-2,3-dimethylphenol
sodium hydrogencarbonate
4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylaniline
Conditions | Yield |
---|---|
With dimethyl sulfoxide | 49% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
2-phenyl-[1,8]naphthyridin-3-ol
Conditions | Yield |
---|---|
With dmap In 1,2-dichloro-benzene at 140℃; for 20h; | 42% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
3,4-dihydro-2H-benzo[b][1,4]oxazin-7-ol hydrochloride
7-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 109h; | 40.5% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
thiophene-2-carboxylic acid (4-hydroxy-phenyl)-amide
thiophene-2-carboxylic acid [4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-amide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 140℃; for 5h; | 36% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
p-benzoylaminophenol
N-[4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-benzamide
Conditions | Yield |
---|---|
at 140℃; for 3h; | 32% |
at 140℃; for 3h; Product distribution / selectivity; | 32% |
at 140℃; for 3h; | 32% |
In N,N-dimethyl-formamide at 145℃; for 7h; Product distribution / selectivity; | 28% |
4-fluoro-2-methyl-1H-indol-5-ol
7-(benzyloxy)-4-chloro-6-methoxyquinoline
7-(benzyloxy)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinoline
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 16h; Inert atmosphere; | 27% |
With dmap In 1,4-dioxane for 72h; Reflux; |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
2-(4-hydroxyphenyl)-1-phenylethan-1-one
2-[4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-1-phenyl-ethanone
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 145℃; for 5h; | 21% |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
sodium 4-aminophenolate
4-(7-benzyloxy-6-methoxyquinolin-4-yloxy)aniline
Conditions | Yield |
---|---|
In ISOPROPYLAMIDE at 120℃; for 22h; |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-acetaminophenol
N-[4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-acetamide
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 150℃; for 2h; |
7-(benzyloxy)-4-chloro-6-methoxyquinoline
6-hydroxy-1-naphthoic acid
6-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-1-naphthoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 130℃; for 5h; |
Conditions | Yield |
---|---|
With dmap In 1,4-dioxane for 72h; Heating / reflux; |
5-amino-1H-indole
7-(benzyloxy)-4-chloro-6-methoxyquinoline
4-(1H-indol-5-ylamino)-7-benzyloxy-6-methoxy-quinoline
Conditions | Yield |
---|---|
In isopropyl alcohol for 1h; Heating / reflux; |
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