Conditions | Yield |
---|---|
In paraffin oil at 230℃; for 0.833333h; Temperature; Solvent; | 98.5% |
at 250 - 270℃; oder in einem Gemisch von Diphenylaether und Biphenyl; | |
In diphenylether for 1h; Heating; | |
In water at 150 - 170℃; for 5h; Autoclave; | 480 kg |
7-chloro-1,2,3,4-tetrahydroquinolin-4-one
A
7-chloro-4-hydroxylquinoline
B
quinolin-4-ol
Conditions | Yield |
---|---|
A 88.3% B n/a |
4,7-dichloroquinoline
A
quinoline
B
7-chloroquinoline
C
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With triethylsilane; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 70℃; for 18h; chemoselective reaction; | A 5% B 85% C 8% |
With triethylsilane; Pd(PPh3)2Cl2; water In acetonitrile at 70℃; for 18h; chemoselective reaction; | A 5% B 85% C 8% |
7-chloro-4-methoxyquinoline
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With water; hydrogen bromide; Aliquat 336 at 105℃; for 4h; Catalytic behavior; | 85% |
N-p-toluenesulfonyl-4-(t-butyldimethylsilyloxy)-7-chloro-1,2-dihydroquinoline
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With sodium hydroxide In methanol Heating; | 81% |
2-(3-chlorophenylamino)methylenemalonic acid diethyl ester
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With dowtherm for 4h; | 49.7% |
In diphenylether; biphenyl at 240℃; for 4h; | 49.7% |
Multi-step reaction with 3 steps 1: diphenyl ether / 1 h / Heating 2: 2 N aq. NaOH / 1 h / Heating 3: diphenyl ether / 1 h / Heating View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetonitrile at 70℃; for 18h; | 15% |
With tetraethylammonium iodide; oxygen In N,N-dimethyl-formamide electrolysis, C-anode, Hg-cathode; | 4% |
With acetic acid | |
Multi-step reaction with 2 steps 1: acetic acid / 1 h / 125 °C 2: sodium hydroxide View Scheme |
7-chloro-1,2,3,4-tetrahydroquinolin-4-one
7-chloro-4-hydroxylquinoline
7-chlorokynurenic acid
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With 1-Chloronaphthalene | |
With mineral oil at 270℃; |
Conditions | Yield |
---|---|
With sodium hydroxide; ethanol; water | |
With hydrogenchloride; water |
A
7-chloro-4-hydroxylquinoline
B
5-chloro-4-hydroxyquinoline
Conditions | Yield |
---|---|
With diphenylether |
7-amino-quinolin-4-ol
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid; sodium nitrite Erwaermen der Diazoniumsalz-Loesung mit Kupfer(I)-chlorid und wss. Salzsaeure.; |
5-[(3-chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione
A
7-chloro-4-hydroxylquinoline
B
5-chloro-4-hydroxyquinoline
Conditions | Yield |
---|---|
In diphenylether at 300℃; for 0.0833333h; microwave irradiation; |
cycl-isopropylidene malonate
3-chloro-aniline
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Stage #1: cycl-isopropylidene malonate With orthoformic acid triethyl ester at 145℃; Stage #2: 3-chloro-aniline at 50 - 145℃; Stage #3: In diphenylether at 250℃; |
2-acetyl-5-chloroaniline
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 75 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 95 percent / K2CO3 / dimethylformamide / 1 h / 80 °C 3: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 4: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 5: 81 percent / aq. NaOH / methanol / Heating View Scheme | |
Multi-step reaction with 2 steps 2: NaOH-solution; ethanol; water View Scheme |
N-(2-acetyl-5-chlorophenyl)-4-methylbenzenesulfonamide
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / K2CO3 / dimethylformamide / 1 h / 80 °C 2: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 3: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 4: 81 percent / aq. NaOH / methanol / Heating View Scheme |
N-allyl-N-p-toluenesulfonyl-2-acetyl-5-chloroaniline
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 2: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 3: 81 percent / aq. NaOH / methanol / Heating View Scheme |
N-allyl-N-p-toluenesulfonyl-2-[1-(tert-butyldimethylsilyloxy)vinyl]-5-chloroaniline
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 2: 81 percent / aq. NaOH / methanol / Heating View Scheme |
7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2 N aq. NaOH / 1 h / Heating 2: diphenyl ether / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: aqueous NaOH 2: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydroxide; water / diphenylether / 0.5 h 2: paraffin oil / 0.83 h / 230 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.5 h / 165 °C 2: diphenyl ether / 1 h / Heating 3: 2 N aq. NaOH / 1 h / Heating 4: diphenyl ether / 1 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: diphenyl ether View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / Erhitzen des Reaktionsprodukts in Paraffinoel auf 250grad 2: aqueous NaOH 3: mineral oil / 270 °C View Scheme | |
Multi-step reaction with 4 steps 3: aqueous NaOH 4: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl View Scheme |
7-amino-4-hydroxy-quinoline-3-carboxylic acid
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenyl ether / 225 - 245 °C 2: acetic acid; sodium nitrite; sulfuric acid / Erwaermen der Diazoniumsalz-Loesung mit Kupfer(I)-chlorid und wss. Salzsaeure. View Scheme |
7-chloro-4-hydroxy-quinoline-2-carboxylic acid ethyl ester
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: mineral oil / 270 °C View Scheme | |
Multi-step reaction with 2 steps 1: aqueous NaOH 2: 1-chloro-naphthalene View Scheme |
ethyl α-ethoxycarbonyl-β-(m-nitroanilino)acrylate
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: iron-powder; aqueous acetic acid / Erwaermen des Reaktionsprodukts mit wss. NaOH 3: diphenyl ether / 225 - 245 °C 4: acetic acid; sodium nitrite; sulfuric acid / Erwaermen der Diazoniumsalz-Loesung mit Kupfer(I)-chlorid und wss. Salzsaeure. View Scheme |
7-nitro-4-hydroxy-quinoline-3-carboxylic acid ethylester
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: iron-powder; aqueous acetic acid / Erwaermen des Reaktionsprodukts mit wss. NaOH 2: diphenyl ether / 225 - 245 °C 3: acetic acid; sodium nitrite; sulfuric acid / Erwaermen der Diazoniumsalz-Loesung mit Kupfer(I)-chlorid und wss. Salzsaeure. View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 110 °C 3: iron-powder; aqueous acetic acid / Erwaermen des Reaktionsprodukts mit wss. NaOH 4: diphenyl ether / 225 - 245 °C 5: acetic acid; sodium nitrite; sulfuric acid / Erwaermen der Diazoniumsalz-Loesung mit Kupfer(I)-chlorid und wss. Salzsaeure. View Scheme |
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With sodium hydroxide | 9.07 g |
4'-chloro-2'-nitroacetophenone
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-d6-formamide / 6 h / 80 °C 2: iron; acetic acid / 4 h / 90 °C View Scheme |
7-chloro-4-hydroxylquinoline
Conditions | Yield |
---|---|
With iron; acetic acid at 90℃; for 4h; | 14 g |
Conditions | Yield |
---|---|
With trichlorophosphate for 1h; Heating; | 94% |
With trichlorophosphate Reflux; | 89.5% |
With trichlorophosphate for 2h; Heating / reflux; | 88.5% |
7-chloro-4-hydroxylquinoline
benzoyl chloride
7-chloroquinolin-4-yl benzoate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In dichloromethane at 10 - 25℃; | 94% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 50℃; for 4h; | 94% |
7-chloro-4-hydroxylquinoline
methyl-phenyl-carbamic acid 7-chloro-quinolin-4-yl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile | 93% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 10h; | 92% |
7-chloro-4-hydroxylquinoline
3,7-dichloroquinolin-4-ol
Conditions | Yield |
---|---|
With N-chloro-succinimide; acetic acid at 60℃; for 5h; | 88% |
7-chloro-4-hydroxylquinoline
7-chloro-3-bromoquinolin-4-ol
Conditions | Yield |
---|---|
With N-Bromosuccinimide; acetic acid at 60℃; for 5h; | 88% |
7-chloro-4-hydroxylquinoline
7-chloro-3-iodoquinolin-4-ol
Conditions | Yield |
---|---|
With N-iodo-succinimide; acetic acid at 60℃; for 5h; | 87% |
With iodine; N-butylamine; potassium iodide In water; N,N-dimethyl-formamide at 20℃; for 36h; | 59% |
With Iodine monochloride; acetic acid |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; for 1h; | 82% |
Conditions | Yield |
---|---|
With nitric acid; propionic acid at 125℃; | 79% |
With nitric acid; propionic acid at 90℃; for 3h; Reflux; | 74% |
With nitric acid; propionic acid for 1.25h; Reflux; | 70% |
7-chloro-4-hydroxylquinoline
(2,6-dimethylphenyl)-λ3-iodanediyl diacetate
Conditions | Yield |
---|---|
Stage #1: 7-chloro-4-hydroxylquinoline; (2,6-dimethylphenyl)-λ3-iodanediyl diacetate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 6h; Inert atmosphere; Schlenk technique; Stage #2: With palladium diacetate; caesium carbonate; triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 30h; Schlenk technique; Inert atmosphere; Molecular sieve; | 78% |
7-chloro-4-hydroxylquinoline
N,N-phenylbistrifluoromethane-sulfonimide
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide Ambient temperature; | 75% |
7-chloro-4-hydroxylquinoline
7-chloro-4-bromo-quinoline
Conditions | Yield |
---|---|
With phosphorus tribromide In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; | 70% |
With phosphorus tribromide In N,N-dimethyl-formamide at 20℃; for 0.5h; | 57% |
With phosphorus tribromide In N,N-dimethyl-formamide at 60℃; | 56% |
Stage #1: 7-chloro-4-hydroxylquinoline With dibromotriphenylphosphorane In acetonitrile for 16h; Reflux; Stage #2: With sodium hydroxide In dichloromethane; water | |
With phosphorus tribromide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; |
7-chloro-4-hydroxylquinoline
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O-(7-chloro-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h; | A n/a B 69% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione In dimethyl sulfoxide at 120℃; for 24h; | 69% |
7-chloro-4-hydroxylquinoline
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester
(2S,4R)-N-Boc-4-(7-chloro-quinolin-4-yloxy)-proline methyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 30h; | 68% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 30h; | 68% |
7-chloro-4-hydroxylquinoline
methyl 4-hydroxy-4-methyl-2-pentynoate
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; lithium trifluoromethanesulfonate In 1,2-dimethoxyethane at 100℃; for 12h; Schlenk technique; Inert atmosphere; | 64% |
7-chloro-4-hydroxylquinoline
7-chloro-4-(4-{3-[(7-chloroquinolin-4-yl)oxyl]propyl}piperazin-1-yl)quinoline
Conditions | Yield |
---|---|
With sodium hydroxide In water for 14h; Reflux; | 59.4% |
7-chloro-4-hydroxylquinoline
7-chloro-4-[4-(3-chloropropyl)piperazin-1-yl]quinoline
7-chloro-4-(4-{3-[(7-chloroquinolin-4-yl)oxyl]propyl}piperazin-1-yl)quinoline
Conditions | Yield |
---|---|
With sodium hydroxide In water for 14h; Reflux; | 59.14% |
Conditions | Yield |
---|---|
With silver carbonate In toluene for 1h; Heating; | 58% |
7-chloro-4-hydroxylquinoline
5-diethylamino-2-pentylamine
A
4-(4-diethylamino-1-methylbutylamino)-quinoline
B
Chloroquine
Conditions | Yield |
---|---|
With potassium pyrosulfite; palladium 10% on activated carbon; water; ammonium formate at 120℃; for 16h; Inert atmosphere; Schlenk technique; | A 12% B 56% |
formaldehyd
7-chloro-4-hydroxylquinoline
ethylamine
Bis(7-chloro-4-hydroxy-3-quinolylmethyl)benzylamine
Conditions | Yield |
---|---|
In diethyl ether for 20h; Heating; | 55% |
7-chloro-4-hydroxylquinoline
5-(bromomethyl)-3-isoxazolecarboxylic acid ethyl ester
5-[[(7-chloroquinolin-4-yl)oxy]methyl]-isoxazole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 7-chloro-4-hydroxylquinoline With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: 5-(bromomethyl)-3-isoxazolecarboxylic acid ethyl ester In acetone Reflux; | 54% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 24h; Inert atmosphere; stereoselective reaction; | 44% |
Molecular Structure of 7-Chloroquinolin-4-ol (CAS NO.86-99-7):
IUPAC Name: 7-chloro-1H-quinolin-4-one
Empirical Formula: C9H6ClNO
Molecular Weight: 179.603
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 20.31Å2
Index of Refraction: 1.608
Molar Refractivity: 46.4 cm3
Molar Volume: 134 cm3
Surface Tension: 46.8 dyne/cm
Density: 1.339 g/cm3
Flash Point: 136.9 °C
Enthalpy of Vaporization: 54.31 kJ/mol
Boiling Point: 302.8 °C at 760 mmHg
Vapour Pressure: 0.000966 mmHg at 25°C
Melting point: 276-279 °C(lit.)
BRN: 125356
InChI
InChI=1/C9H6ClNO/c10-6-1-2-7-8(5-6)11-4-3-9(7)12/h1-5H,(H,11,12)
Smiles
c12c(cc(cc1)Cl)nccc2O
EINECS: 201-715-2
Product Categories: Quinolines, Quinazolines and derivatives; Quinolines; Haloquinolines; Hydroxyquinolines
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
7-Chloroquinolin-4-ol , with CAS number of 86-99-7, can be called 4-quinolinol, 7-chloro- ; 7-Chloro-4-Hydroxyquinoline ; 7-Chloro-4-quinolinol .
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