Product Name

  • Name

    2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol

  • EINECS 204-249-8
  • CAS No. 118-42-3
  • Article Data27
  • CAS DataBase
  • Density 1.177 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 118-42-3 (2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol)
  • Hazard Symbols
  • 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;
  • PSA 48.39000
  • LogP 3.85600

Synthetic route

Plaquenil

Plaquenil

hydroxychloroquine
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
4,7-dichloroquinoline
86-98-6

4,7-dichloroquinoline

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

rac-5--2-pentanamine

hydroxychloroquine
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%
2,3-dichloroquinoline
613-18-3

2,3-dichloroquinoline

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

rac-5--2-pentanamine

hydroxychloroquine
118-42-3

hydroxychloroquine

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

hydroxychloroquine hydrochloride

hydroxychloroquine
118-42-3

hydroxychloroquine

Conditions
ConditionsYield
With sodium t-butanolate In isopropyl alcohol Solvent; Reagent/catalyst;88.3%
7-chloro-4-fluoroquinoline
103526-68-7

7-chloro-4-fluoroquinoline

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

rac-5--2-pentanamine

hydroxychloroquine
118-42-3

hydroxychloroquine

Conditions
ConditionsYield
In acetonitrile for 3h;88.3%
4,7-dichloroquinoline
86-98-6

4,7-dichloroquinoline

(+-)-2--ethanol

(+-)-2--ethanol

hydroxychloroquine
118-42-3

hydroxychloroquine

Conditions
ConditionsYield
With phenol at 125 - 130℃;
With potassium iodide; phenol
5-(N-ethyl-N-2-hydroxyethylamine)-2-pentanone
74509-79-8

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

hydroxychloroquine
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
5-iodo-2-pentanone
3695-29-2

5-iodo-2-pentanone

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

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

hydroxychloroquine
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
4,7-dichloroquinoline
86-98-6

4,7-dichloroquinoline

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

rac-5--2-pentanamine

hydroxychloroquine
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
hydroxychloroquine
118-42-3

hydroxychloroquine

Plaquenil

Plaquenil

Conditions
ConditionsYield
With sulfuric acid In water at 15 - 55℃; for 5h; Temperature; Solvent;98%
With sulfuric acid In ethanol at 5 - 10℃; for 12h; Large scale;98.6%
With sulfuric acid In ethanol at 0 - 30℃; for 5h; pH=4.5 - 5.5; Solvent;96.1%
1-ethenesulfonyl-piperidine
66089-45-0

1-ethenesulfonyl-piperidine

hydroxychloroquine
118-42-3

hydroxychloroquine

N4-(7-chloroquinolin-4-yl)-N1-ethyl-N1-(2-(2-(piperidin-1-ylsulfonyl)ethoxy)ethyl)pentane-1,4-diamine

N4-(7-chloroquinolin-4-yl)-N1-ethyl-N1-(2-(2-(piperidin-1-ylsulfonyl)ethoxy)ethyl)pentane-1,4-diamine

Conditions
ConditionsYield
Stage #1: hydroxychloroquine With silver(I) acetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at -20℃; Inert atmosphere;
Stage #2: 1-ethenesulfonyl-piperidine With potassium hexamethylsilazane In tetrahydrofuran; N,N-dimethyl-formamide at -20℃; for 9h; Inert atmosphere; regioselective reaction;		92%
2,2,2-trifluoroethyl benzoate
1579-72-2

2,2,2-trifluoroethyl benzoate

hydroxychloroquine
118-42-3

hydroxychloroquine

2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethyl benzoate

2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethyl benzoate

Conditions
ConditionsYield
With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] In toluene at 120℃; for 5h; Inert atmosphere; Schlenk technique; chemoselective reaction;89%
hydroxychloroquine
118-42-3

hydroxychloroquine

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

C22H28ClN5O2

C22H28ClN5O2

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Schlenk technique;75%
hydroxychloroquine
118-42-3

hydroxychloroquine

C18H25ClN6

C18H25ClN6

Conditions
ConditionsYield
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 48h; Inert atmosphere;70%
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;
hydroxychloroquine
118-42-3

hydroxychloroquine

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

rac-N1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N4-(7-chloroquinolin-4-yl)-N1-ethylpentane-1,4-diamine

rac-N1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N4-(7-chloroquinolin-4-yl)-N1-ethylpentane-1,4-diamine

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 20℃; for 48h;68%
hydroxychloroquine
118-42-3

hydroxychloroquine

(R)-Hydroxychloroquine

(R)-Hydroxychloroquine

Conditions
ConditionsYield
Stage #1: hydroxychloroquine With (S)-Malic acid In ethanol; ethyl acetate at 0 - 5℃; for 0.5h;
Stage #2: With sodium methylate In methanol at 0 - 20℃; for 0.5h; Reagent/catalyst; Solvent;		64%
hydroxychloroquine
118-42-3

hydroxychloroquine

(S)-Hydroxychloroquine

(S)-Hydroxychloroquine

Conditions
ConditionsYield
Stage #1: hydroxychloroquine With D-Malic acid In ethanol; ethyl acetate at 0 - 5℃; for 0.5h;
Stage #2: With sodium methylate In methanol at 0 - 20℃; for 0.5h; Reagent/catalyst; Solvent;		56%
hydroxychloroquine
118-42-3

hydroxychloroquine

acrylonitrile
107-13-1

acrylonitrile

3-(2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethoxy)propanenitrile
1606176-75-3

3-(2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethoxy)propanenitrile

Conditions
ConditionsYield
With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; 1,2-bis-(diphenylphosphino)ethane In hexane; N,N-dimethyl-formamide at 20℃; for 3h; Michael Addition; Inert atmosphere; chemoselective reaction;56%
hydroxychloroquine
118-42-3

hydroxychloroquine

6‐(3‐methyl‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)hexanoic acid
84978-05-2

6‐(3‐methyl‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)hexanoic acid

2-[4-[(7-chloro-4-quinolyl)amino]pentyl(ethyl)amino]ethyl-6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoate

2-[4-[(7-chloro-4-quinolyl)amino]pentyl(ethyl)amino]ethyl-6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;53%
(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

hydroxychloroquine
118-42-3

hydroxychloroquine

hydroxychloroquine linolenate

hydroxychloroquine linolenate

Conditions
ConditionsYield
Stage #1: (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Cooling with ice; Inert atmosphere;
Stage #2: hydroxychloroquine In dichloromethane at 20℃; for 12h; Reagent/catalyst; Inert atmosphere;		52.5%
4,7-dichloroquinoline
86-98-6

4,7-dichloroquinoline

hydroxychloroquine
118-42-3

hydroxychloroquine

C27H30Cl2N4O

C27H30Cl2N4O

Conditions
ConditionsYield
With potassium tert-butylate at 110 - 115℃; for 4h;50.3%
tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

hydroxychloroquine
118-42-3

hydroxychloroquine

C25H38ClN3O3

C25H38ClN3O3

Conditions
ConditionsYield
With silver(I) acetate; sodium hexamethyldisilazane; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at -20℃; chemoselective reaction;33%
succinic acid anhydride
108-30-5

succinic acid anhydride

hydroxychloroquine
118-42-3

hydroxychloroquine

hydroxychloroquine-succinate
1057094-59-3

hydroxychloroquine-succinate

Conditions
ConditionsYield
With dmap; sodium sulfate In pyridine at 20℃; for 6h;
hydroxychloroquine
118-42-3

hydroxychloroquine

2-cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite

2-cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite

hydroxychloroquine phosphoramidite

hydroxychloroquine phosphoramidite

Conditions
ConditionsYield
With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 1.5 - 2h;
hydroxychloroquine
118-42-3

hydroxychloroquine

C18H24ClN3O

C18H24ClN3O

Conditions
ConditionsYield
pH=8; Electrochemical reaction;
hydroxychloroquine
118-42-3

hydroxychloroquine

rac-(9-(7-chloroquinolin-4-yl)-14-ethyl-16-hydroxy-10-methyl-3,8-dioxo-7-oxa-2,9,14-triazahexadecane-1,1-diyl)diphosphonic acid

rac-(9-(7-chloroquinolin-4-yl)-14-ethyl-16-hydroxy-10-methyl-3,8-dioxo-7-oxa-2,9,14-triazahexadecane-1,1-diyl)diphosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / 1,2-dichloro-ethane / 48 h / 20 °C
2.1: potassium carbonate / dichloromethane / 2 h / 0 °C
2.2: 36 h / 0 - 20 °C
View Scheme
(4-biphenylyl)acetic acid
5728-52-9

(4-biphenylyl)acetic acid

hydroxychloroquine
118-42-3

hydroxychloroquine

HBA

HBA

Conditions
ConditionsYield
Stage #1: (4-biphenylyl)acetic acid With 1,1'-carbonyldiimidazole In chloroform at 20℃; for 2 - 5h;
Stage #2: hydroxychloroquine In chloroform at 70℃; for 10 - 12h; Reflux;
hydroxychloroquine
118-42-3

hydroxychloroquine

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

HIN

HIN

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In chloroform at 20℃; for 2 - 5h;
Stage #2: hydroxychloroquine In chloroform at 70℃; for 10 - 12h; Reflux;
hydroxychloroquine
118-42-3

hydroxychloroquine

aceclofenac
89796-99-6

aceclofenac

HA

HA

Conditions
ConditionsYield
Stage #1: aceclofenac With 1,1'-carbonyldiimidazole In chloroform at 20℃; for 2 - 5h;
Stage #2: hydroxychloroquine In chloroform at 70℃; for 10 - 12h; Reflux;
[2-(2,6-dichloroanilino)phenyl]acetic acid
15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

hydroxychloroquine
118-42-3

hydroxychloroquine

HD

HD

Conditions
ConditionsYield
Stage #1: [2-(2,6-dichloroanilino)phenyl]acetic acid With 1,1'-carbonyldiimidazole In chloroform at 20℃; for 2 - 5h;
Stage #2: hydroxychloroquine In chloroform at 70℃; for 10 - 12h; Reflux;
hydroxychloroquine
118-42-3

hydroxychloroquine

licofelone
156897-06-2

licofelone

HL

HL

Conditions
ConditionsYield
Stage #1: licofelone With 1,1'-carbonyldiimidazole In chloroform at 20℃; for 2 - 5h;
Stage #2: hydroxychloroquine In chloroform at 70℃; for 10 - 12h; Reflux;

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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