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Hydroxychloroquine
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Name

Hydroxychloroquine

 EINECS 204-249-8
CAS No. 118-42-3 Density 1.177 g/cm3
PSA 48.39000 LogP 3.85600
Solubility N/A Melting Point 89-91°
Formula C18H26ClN3O Boiling Point 516.673 °C at 760 mmHg
Molecular Weight 335.877 Flash Point 266.275 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 118-42-3 (2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol) Hazard Symbols N/A
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;

Article Data 27

Hydroxychloroquine Synthetic route

Plaquenil

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
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
86-98-6

4,7-dichloroquinoline

69559-11-1

rac-5--2-pentanamine

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
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%
613-18-3

2,3-dichloroquinoline

69559-11-1

rac-5--2-pentanamine

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
In ethylene glycol at 90 - 100℃; for 24h; Temperature; Large scale;92.3%

hydroxychloroquine hydrochloride

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
With sodium t-butanolate In isopropyl alcohol Solvent; Reagent/catalyst;88.3%
103526-68-7

7-chloro-4-fluoroquinoline

69559-11-1

rac-5--2-pentanamine

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
In acetonitrile for 3h;88.3%
86-98-6

4,7-dichloroquinoline

(+-)-2--ethanol

(+-)-2--ethanol

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
With phenol at 125 - 130℃;
With potassium iodide; phenol
74509-79-8

5-(N-ethyl-N-2-hydroxyethylamine)-2-pentanone

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
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
3695-29-2

5-iodo-2-pentanone

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
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
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
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
86-98-6

4,7-dichloroquinoline

118-42-3

hydroxychloroquine

Conditions
ConditionsYield
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

Hydroxychloroquine Chemical Properties

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

Hydroxychloroquine Uses

Plaquenil is anti-malarial drugs commonly used for the treatment of lupus erythematosus and rheumatoid arthritis.

Hydroxychloroquine Toxicity Data With Reference

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.

Hydroxychloroquine Safety Profile

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.

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