Conditions | Yield |
---|---|
With aluminum (III) chloride; N-chloro-succinimide In dichloromethane at 35℃; for 8h; Temperature; Solvent; Darkness; Green chemistry; | 98.8% |
With hydrogenchloride; chlorine In water Reagent/catalyst; Inert atmosphere; Darkness; | 98.9% |
With hydrogenchloride; sodium hypochlorite In water at 20 - 30℃; for 4.5h; Temperature; | 97.7% |
5,7-dichloro-8-hydroxyquinoline 1-oxide
methylmagnesium chloride
chloroquinaldol
Conditions | Yield |
---|---|
With copper(l) chloride; magnesium chloride In diethyl ether at 23℃; for 12h; Grignard Reaction; Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
With acetic acid for 3h; Cooling with ice; |
chloroquinaldol
5,7-dichloro-8-hydroxy-2-quinolinecarboxaldehyde
Conditions | Yield |
---|---|
With selenium(IV) oxide In 1,4-dioxane at 50 - 80℃; for 3h; | 100% |
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 12h; | 80% |
With selenium(IV) oxide In 1,4-dioxane at 55 - 80℃; | 2.1 g |
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 12h; |
chloroquinaldol
Conditions | Yield |
---|---|
Stage #1: chloroquinaldol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; | 97% |
Stage #1: chloroquinaldol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere; | 97% |
chloroquinaldol
tert-butylphenylphosphinic acid chloride
5,7-dichloro-2-methylquinolin-8-yl tert-butyl(phenyl)posphinate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 24h; Reflux; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
In ethanol; acetone at 85℃; for 5h; Solvent; Temperature; | 95.3% |
chloroquinaldol
Conditions | Yield |
---|---|
In methanol; dichloromethane at 65℃; for 6h; Reflux; | 95.2% |
chloroquinaldol
cis-dichlorobis(dimethylsulfoxide)platinum(II)
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 80℃; for 12h; Solvent; Temperature; | 95% |
Conditions | Yield |
---|---|
Stage #1: chloroquinaldol With potassium tert-butylate In tetrahydrofuran for 3h; Reflux; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; | 94% |
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran at 40℃; for 30h; | 83% |
chloroquinaldol
3,5-dihydroxybenzaldehyde
5,7-dichloro-2-[2-(3,5-dihydroxyphenyl)vinyl]quinolin-8-ol
Conditions | Yield |
---|---|
Stage #1: chloroquinaldol; 3,5-dihydroxybenzaldehyde With acetic anhydride for 24h; Reflux; Stage #2: With pyridine In water for 3h; Reflux; | 93% |
chloroquinaldol
2-hydroxy-5-acetyloxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: chloroquinaldol; 2-hydroxy-5-acetyloxybenzaldehyde With acetic anhydride for 24h; Reflux; Stage #2: With pyridine In water for 3h; Reflux; | 93% |
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
chloroquinaldol
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; under 760.051 Torr; for 12h; | 93% |
chloroquinaldol
5-acetoxy-2-nitro-benzaldehyde
Conditions | Yield |
---|---|
at 150℃; | 92% |
chloroquinaldol
acetic anhydride
8-acetoxy-5,7-dichloro-2-methylquinoline
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 6h; | 91% |
chloroquinaldol
Conditions | Yield |
---|---|
With water-d2; benzoic acid at 120℃; for 4h; | 91% |
With water-d2; benzoic acid at 120℃; for 16h; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
at 150℃; | 91% |
chloroquinaldol
benzyl bromide
8-(benzyloxy)-5,7-dichloro-2-methylquinoline
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 5h; Reflux; | 91% |
Conditions | Yield |
---|---|
With acetic acid at 130℃; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
In methanol; acetonitrile at 80℃; for 24h; | 90.8% |
Conditions | Yield |
---|---|
In methanol; acetonitrile at 80℃; for 24h; | 90.5% |
Conditions | Yield |
---|---|
In ethanol; water at 70℃; for 12h; Solvent; Temperature; | 90.21% |
sodium tetrafluoroborate
chloroquinaldol
[(η6-hexamethylbenzene)Ru(η2-N,O-5,7-dichloro-2-methyl-8-hydroxyquinolate)(H2O)]BF4
Conditions | Yield |
---|---|
With Ag2SO4 In water under inert atm.; mixt. of ((C6(CH3)6)RuCl2)2 (0.082 mmol) and Ag2SO4 (0.163 mmol) in H2O stirred for 2 h in dark at room temp., soln. filtered,NC9H3Cl2MeOH (0.163 mmol) added, stirred for 2 h in dark at room temp., pptd. by satd. aq. soln. of NaBF4; crystd. from H2O; elem. anal.; | 90% |
chloroquinaldol
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; | 90% |
With dmap; triethylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; | 90% |
dipyridil[3,2-a:2',3'-c]phenazine
chloroquinaldol
Conditions | Yield |
---|---|
In methanol; acetonitrile at 80℃; for 24h; | 89.2% |
Conditions | Yield |
---|---|
at 80℃; for 72h; | 89.11% |
Conditions | Yield |
---|---|
With acetic acid at 130℃; Inert atmosphere; | 88% |
chloroquinaldol
salicylaldehyde
5,7-dichloro-2-[2-(2-hydroxyphenyl)vinyl]quinolin-8-ol
Conditions | Yield |
---|---|
Stage #1: chloroquinaldol; salicylaldehyde With acetic anhydride for 24h; Reflux; Stage #2: With pyridine In water for 3h; Reflux; | 87% |
Conditions | Yield |
---|---|
In toluene at 24.84℃; for 16h; Inert atmosphere; | 87% |
chloroquinaldol
5,7-dichloro-8-hydroxy-2-methylquinoline 1-oxide
Conditions | Yield |
---|---|
With phosphoric acid; dihydrogen peroxide; molybdenum(VI) oxide In water; acetonitrile at 50℃; | 87% |
Conditions | Yield |
---|---|
at 150℃; | 87% |
chloroquinaldol
2-nitroveratraldehyde
Conditions | Yield |
---|---|
at 150℃; | 87% |
1. | orl-rat LD50:660 mg/kg | 29ZVAB Handbook of Analytical Toxicology ,Sunshine, I., ed.,Cleveland, OH.: Chemical Rubber Co.,1969,33. | ||
2. | orl-dog LD50:2250 mg/kg | 29ZVAB Handbook of Analytical Toxicology ,Sunshine, I., ed.,Cleveland, OH.: Chemical Rubber Co.,1969,33. | ||
3. | orl-rbt LD50:160 mg/kg | 29ZVAB Handbook of Analytical Toxicology ,Sunshine, I., ed.,Cleveland, OH.: Chemical Rubber Co.,1969,33. |
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