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CAS No.: | 118-42-3 |
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Name: | 2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C18H26ClN3O |
Molecular Weight: | 335.877 |
Synonyms: | Ethanol,2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]- (6CI,8CI);7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline;7-Chloro-4-[4-[ethyl(2-hydroxyethyl)amino]-1-methylbutylamino]quinoline;7-Chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline;Hydroxychloroquine;Oxichloroquine;Oxychlorochin;RacemicHydroxychloroquine;WIN 1258;Win 1258-2; |
EINECS: | 204-249-8 |
Density: | 1.177 g/cm3 |
Melting Point: | 89-91° |
Boiling Point: | 516.673 °C at 760 mmHg |
Flash Point: | 266.275 °C |
PSA: | 48.39000 |
LogP: | 3.85600 |
hydroxychloroquine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; Cooling with ice; | 97.6% |
With sodium hydroxide In water; ethyl acetate at 0℃; for 1h; | 91% |
With sodium hydroxide In water at 0℃; for 0.5h; | 91% |
With ammonia In chloroform at 20℃; for 1h; pH=9; | 90% |
With ammonium hydroxide In water |
Conditions | Yield |
---|---|
With KF/Al2O3 In toluene at 110 - 120℃; for 12h; Reagent/catalyst; Solvent; Temperature; Large scale; | 94% |
With sodium hydroxide at 140℃; for 6h; pH=7 - Ca. 8; Temperature; pH-value; Inert atmosphere; | 91.2% |
at 78 - 130℃; for 8.33333h; Temperature; Inert atmosphere; | 90.3% |
Conditions | Yield |
---|---|
In ethylene glycol at 90 - 100℃; for 24h; Temperature; Large scale; | 92.3% |
hydroxychloroquine
Conditions | Yield |
---|---|
With sodium t-butanolate In isopropyl alcohol Solvent; Reagent/catalyst; | 88.3% |
Conditions | Yield |
---|---|
In acetonitrile for 3h; | 88.3% |
Conditions | Yield |
---|---|
With phenol at 125 - 130℃; | |
With potassium iodide; phenol |
5-(N-ethyl-N-2-hydroxyethylamine)-2-pentanone
hydroxychloroquine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; hydroxylamine / tetrahydrofuran / 0.17 h / 100 °C / Inert atmosphere; Flow reactor 2: hydrogen / tetrahydrofuran / 4 h / 80 °C / 7500.75 Torr / Inert atmosphere; Flow reactor 3: potassium carbonate; triethylamine / ethanol / 6 h / 125 °C / Inert atmosphere; Flow reactor View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / tetrahydrofuran / 0.17 h / 80 - 100 °C / Flow reactor; Inert atmosphere 2: potassium carbonate; hydroxylamine / tetrahydrofuran / 0.17 h / 100 °C / Inert atmosphere; Flow reactor 3: hydrogen / tetrahydrofuran / 4 h / 80 °C / 7500.75 Torr / Inert atmosphere; Flow reactor 4: potassium carbonate; triethylamine / ethanol / 6 h / 125 °C / Inert atmosphere; Flow reactor View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / tetrahydrofuran / Flow reactor; Inert atmosphere 1.2: 100 °C / Flow reactor; Inert atmosphere 2.1: hydrogen / tetrahydrofuran / 80 °C / 7500.75 Torr 3.1: potassium carbonate; triethylamine / ethanol / 6 h / 125 °C / 775.74 Torr / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: hydrogen iodide / water / 0.08 h / 80 °C / 2250.23 Torr / Inert atmosphere; Flow reactor 2: potassium carbonate / tetrahydrofuran / 0.17 h / 80 - 100 °C / Flow reactor; Inert atmosphere 3: potassium carbonate; hydroxylamine / tetrahydrofuran / 0.17 h / 100 °C / Inert atmosphere; Flow reactor 4: hydrogen / tetrahydrofuran / 4 h / 80 °C / 7500.75 Torr / Inert atmosphere; Flow reactor 5: potassium carbonate; triethylamine / ethanol / 6 h / 125 °C / Inert atmosphere; Flow reactor View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; hydrogen iodide / water / 80 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran / Flow reactor; Inert atmosphere 2.2: 100 °C / Flow reactor; Inert atmosphere 3.1: hydrogen / tetrahydrofuran / 80 °C / 7500.75 Torr 4.1: potassium carbonate; triethylamine / ethanol / 6 h / 125 °C / 775.74 Torr / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 19 h / 110 - 130 °C 2: sodium t-butanolate / isopropyl alcohol View Scheme | |
Multi-step reaction with 2 steps 1: cetyltrimethylammonim bromide; potassium fluoride / acetonitrile / 2 h / 80 °C / Inert atmosphere 2: acetonitrile / 3 h View Scheme |
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Plaquenil has some synonyms like Hydroxychloroquine;2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol;7-chloro-4-(4-(n-ethyl-n-beta-hydroxyethylamino)-1-methylbutylamino)quinolin;7-chloro-4-(5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl)aminoquinoline,and so on.
Molecular Formula: C18H26ClN3O
Molecular Weight: 335.87
EINECS: 204-249-8
1. | orl-mus LD50:1240 mg/kg | JMCMAR Journal of Medicinal Chemistry. 12 (1969),184. | ||
2. | orl-hmn TDLo:429 mg/kg/25D:SKN,BLD | LANCAO Lancet. 1 (1965),1275. | ||
3. | orl-man TDLo:600 mg/kg/25D:GIT | 34ZIAG Toxicology of Drugs and Chemicals Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,321. |
Moderately toxic by ingestion. Human systemic effects by ingestion: dermatitis, gastritis, angranulocytosis. When heated to decomposition it emits very toxic fumes of Cl− and NOx.
Side effects: abdominal cramps, diarrhea, heart problems, reduced appetite, headache, nausea and vomiting.
Overdose symptoms:convulsions, drowsiness, headache, heart problems or heart failure, difficulty breathing and vision problems.