• Name

  ETHYLHYDROCUPREINE

• EINECS
• CAS No. 522-60-1
• Article Data5
• CAS DataBase
• Density 1.18g/cm³
• Solubility
• Melting Point 123-128° when solvent-free
• Formula C21H28 N2 O2
• Boiling Point 508.7°Cat760mmHg
• Molecular Weight 340.466
• Flash Point 261.5°C
• Transport Information
• Appearance
• Safety Poison by ingestion and subcutaneous routes. An eye irritant. When heated to decomposition it emits toxic fumes of NO_x. See also ETHERS.
• Risk Codes R22
• Molecular Structure
• Hazard Symbols Xn
• Synonyms Hydrocinchonidine,6'-ethoxy- (7CI); Hydrocupreine, O6'-ethyl- (8CI); Hydrocupreine, ethyl ether(6CI); Ethylhydrocupreine; Numoquin; Optichin; Optochin
• PSA 45.59000
• LogP 3.72520

Synthetic route

74-96-4

ethyl bromide

5962-19-6

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
Stage #1: (8α,9R)-10,11-dihydro-cinchonan-6',9-diol With caesium carbonate In N,N-dimethyl-formamide for 0.166667h; Stage #2: ethyl bromide In N,N-dimethyl-formamide for 3h;	63%

64-67-5

diethyl sulfate

5962-19-6

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
With potassium hydroxide

75-00-3

chloroethane

5962-19-6

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
With sodium ethanolate at 75℃; im Autoklaven;

O(6')-ethyl-cupreine

O(6')-ethyl-cupreine

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
durch katalytische Hydrierung;

sulfate ethylhydrocupreine-1-oxide

sulfate ethylhydrocupreine-1-oxide

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
With sulphurous acid at 80℃; im Autoklaven;

130-95-0

Quinine

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium on carbon; hydrogen / 72 h 2.1: sodium hydride; ethanethiol / mineral oil; N,N-dimethyl-formamide / 13 h / 100 °C 3.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h 3.2: 3 h View Scheme

522-66-7

dihydroquinine

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride; ethanethiol / mineral oil; N,N-dimethyl-formamide / 13 h / 100 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h 2.2: 3 h View Scheme

7664-93-9

sulfuric acid

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

CrO3

CrO3

525-39-3

6-ethoxy-quinoline-4-carboxylic acid

...Expand

7664-93-9

sulfuric acid

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

potassium nitrate

potassium nitrate

5'-nitro-ethylhydrocupreinesulfuric acid

5'-nitro-ethylhydrocupreinesulfuric acid

...Expand

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

chromium trioxide

chromium trioxide

6-ethoxy-cinchoninic acid chloride

6-ethoxy-cinchoninic acid chloride

Conditions

Conditions	Yield
durch Behandeln mit Thionylchlorid;

7722-84-1

dihydrogen peroxide

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

ethylhydrocupreine-1-oxide

ethylhydrocupreine-1-oxide

7446-08-4

selenium(IV) oxide

7664-93-9

sulfuric acid

522-60-1

(R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline

selenoethylhydrocupreine

selenoethylhydrocupreine

Conditions

Conditions	Yield
folgend Verduennen mit Wasser;

...Expand

Hydrocupreine ethyl ether Chemical Properties

Hydrocupreine ethyl ether Toxicity Data With Reference

Hydrocupreine ethyl ether Safety Profile