Name: 2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
SKU: 118-42-3

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Basic Information

Molecular Structure:
CAS No.:	118-42-3
Name:	2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
Article Data:	27

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

Synthetic route

: Plaquenil

: 118-42-3
hydroxychloroquine

Conditions

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

: 86-98-6
4,7-dichloroquinoline

: 69559-11-1
rac-5--2-pentanamine

: 118-42-3
hydroxychloroquine

Conditions

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%

: 613-18-3
2,3-dichloroquinoline

: 69559-11-1
rac-5--2-pentanamine

: 118-42-3
hydroxychloroquine

Conditions

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

: hydroxychloroquine hydrochloride

: 118-42-3
hydroxychloroquine

Conditions

Conditions	Yield
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

Conditions	Yield
In acetonitrile for 3h;	88.3%

: 86-98-6
4,7-dichloroquinoline

(+-)-2--ethanol: (+-)-2--ethanol

: 118-42-3
hydroxychloroquine

Conditions

Conditions	Yield
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

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

: 3695-29-2
5-iodo-2-pentanone

: 118-42-3
hydroxychloroquine

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

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

: 118-42-3
hydroxychloroquine

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

: 86-98-6
4,7-dichloroquinoline

: 118-42-3
hydroxychloroquine

Conditions

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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Chemistry

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

Uses

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

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.

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 NO_x.

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.