72-80-0

Basic information

• Product Name: 5,7-Dichloro-8-hydroxyquinaldine
• Synonyms: 5,7-Dichloro-2-methyl-8-hydroxyquinoline;5,7-DICHLORO-8-QUINALDOL;5,7-Dichloro-8-hydroxy-2-methylquinoline;5,7-Dichloro-8-hydroxyquinalidine;Chlorquinalol;CHLORQUINALDOL(RG);2-METHYL-5,7-DICHLORO-8-HYDROXYQUINOLINE;5,7-DICHLORO-8-HYDROXYQUINALIDNE
• CAS NO: 72-80-0
• Molecular Formula: C₁₀H₇Cl₂NO
• Molecular Weight: 228.07
• EINECS: 200-789-3
• Product Categories: Pharmaceutical Intermediates;Quinoline&Isoquinoline;Antibiotics;Antibiotics A to Z;Antibiotics A-F;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;SITOSTERAN
• Mol File: 72-80-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 108-112 °C (dec.)(lit.)
• Boiling Point: 350.7 °C at 760 mmHg
• Flash Point: 165.9 °C
• Appearance: yellowish to beige-brown powder
• Density: 1.3126 (rough estimate)
• Vapor Pressure: 2.13E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO, Methaol (Slightly)
• PKA: 2.47±0.30(Predicted)
• Water Solubility: Insoluble
• Merck: 13,2209
• BRN: 156683
• CAS DataBase Reference: 5,7-Dichloro-8-hydroxyquinaldine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-Dichloro-8-hydroxyquinaldine(72-80-0)
• EPA Substance Registry System: 5,7-Dichloro-8-hydroxyquinaldine(72-80-0)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-36/37/38-23/24/25
• Safety Statements: 26-36-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: VC5600000
• Hazardous Substances Data: 72-80-0(Hazardous Substances Data)

Usage

Originator

Sterosan ,Geigy ,US ,1954

Uses

Different sources of media describe the Uses of 72-80-0 differently. You can refer to the following data:
1. Chlorquinaldol is a fungistat and antibacterial agent in topical pharmaceutical preparations (5,7-dichloro-2-methyl-8-quinolinol, Sterosan).
2. antiinfectant, antifungal
3. 5,7-Dichloro-8-hydroxy-2-methylquinoline is an anti-infective agent.

Definition

ChEBI: A monohydroxyquinoline that is quinolin-8-ol which is substituted by a methyl group at position 2 and by chlorine at positions 5 and 7. An antifungal and antibacterial, it was formerly used for topical treatment of skin conditions and vaginal infections.

Manufacturing Process

11.1 parts of 8-hydroxy-quinaldine are dissolved in 140 parts of formic acid. Chlorine is introduced into this solution under cooling, until the increase in weight corresponds to the required quantity of chlorine and a test of the chlorination mixtures gives no more dyestuff formation with diazo-benzene in an acetic acid solutionWhen the chlorination is complete, the reaction mixture is poured into 1,000 parts of water and treated with a dilute sodium bisulfite solution, until no more reaction may be observed with starch potassium iodide paper. Thereby the 5,7-dichloro-8-hydroxy-quinaldine separates out in form of a weakly yellowish colored precipitate. The same is filtered off and thoroughly washed with water.After drying, 15 parts of 5,7-dichloro-8-hydroxy-quinaldine melting at 111°C to 112°C are obtained. When recrystallized from alcohol, the product is obtained in voluminous, slightly yellowish needles having the melting point of 111.5°C to 112°C.

Therapeutic Function

Antibacterial

Purification Methods

Crystallise it from EtOH. [Beilstein 21/3 V 346.]

InChI:InChI=1/C10H7Cl2NO/c1-5-2-3-6-7(11)4-8(12)10(14)9(6)13-5/h2-4,14H,1H3

Synthetic route

2-methyl-8-quinolinol (826-81-3) → chloroquinaldol (72-80-0)

Conditions	Yield
With aluminum (III) chloride; N-chloro-succinimide In dichloromethane at 35℃; for 8h; Temperature; Solvent; Darkness; Green chemistry;	98.8%
With hydrogenchloride; chlorine In water Reagent/catalyst; Inert atmosphere; Darkness;	98.9%
With hydrogenchloride; sodium hypochlorite In water at 20 - 30℃; for 4.5h; Temperature;	97.7%

5,7-dichloro-8-hydroxyquinoline 1-oxide (21168-33-2) + methylmagnesium chloride (676-58-4) → chloroquinaldol (72-80-0)

Conditions	Yield
With copper(l) chloride; magnesium chloride In diethyl ether at 23℃; for 12h; Grignard Reaction; Inert atmosphere;	63%

2-methyl-8-quinolinol (826-81-3) + dichlorohydantoin (4369-36-2) → chloroquinaldol (72-80-0)

Conditions	Yield
With acetic acid for 3h; Cooling with ice;

chloroquinaldol (72-80-0) → 5,7-dichloro-8-hydroxy-2-quinolinecarboxaldehyde (24010-07-9)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane at 50 - 80℃; for 3h;	100%
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 12h;	80%
With selenium(IV) oxide In 1,4-dioxane at 55 - 80℃;	2.1 g
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 12h;

chloroquinaldol (72-80-0) → 5,7-dichloro-2-methyl-quinoline-8-oxysulfonyl fluoride

Conditions	Yield
Stage #1: chloroquinaldol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h;	97%
Stage #1: chloroquinaldol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere;	97%

chloroquinaldol (72-80-0) + tert-butylphenylphosphinic acid chloride (4923-85-7) → 5,7-dichloro-2-methylquinolin-8-yl tert-butyl(phenyl)posphinate (1227180-25-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;	96%

{Ir(mppy)2Cl}2 + chloroquinaldol (72-80-0) → C34H26Cl2IrN3O

Conditions	Yield
In ethanol; acetone at 85℃; for 5h; Solvent; Temperature;	95.3%

diiodo(p-cymene)ruthenium(II) dimer + chloroquinaldol (72-80-0) → [(η6-p-cymene)Ru(2-methyl-5,7-dichloro-8-hydroxyquinolinato)I]

Conditions	Yield
In methanol; dichloromethane at 65℃; for 6h; Reflux;	95.2%

chloroquinaldol (72-80-0) + cis-dichlorobis(dimethylsulfoxide)platinum(II) (75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9) → C12H12Cl3NO2PtS

Conditions	Yield
In methanol; dimethyl sulfoxide at 80℃; for 12h; Solvent; Temperature;	95%

chloroquinaldol (72-80-0) + methyl iodide (74-88-4) → 5,7-dichloro-8-methoxy-2-methylquinoline (1053246-24-4)

Conditions	Yield
Stage #1: chloroquinaldol With potassium tert-butylate In tetrahydrofuran for 3h; Reflux; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;	94%
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran at 40℃; for 30h;	83%

chloroquinaldol (72-80-0) + 3,5-dihydroxybenzaldehyde (26153-38-8) → 5,7-dichloro-2-[2-(3,5-dihydroxyphenyl)vinyl]quinolin-8-ol (1251918-08-7)

Conditions	Yield
Stage #1: chloroquinaldol; 3,5-dihydroxybenzaldehyde With acetic anhydride for 24h; Reflux; Stage #2: With pyridine In water for 3h; Reflux;	93%

chloroquinaldol (72-80-0) + 2-hydroxy-5-acetyloxybenzaldehyde (64418-88-8) → 5,7-dichloro-2-[2-(2-hydroxy-5-acetoxyphenyl)vinyl]quinolin-8-ol

Conditions	Yield
Stage #1: chloroquinaldol; 2-hydroxy-5-acetyloxybenzaldehyde With acetic anhydride for 24h; Reflux; Stage #2: With pyridine In water for 3h; Reflux;	93%

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] (12354-84-6, 12354-85-7) + chloroquinaldol (72-80-0) → C20H21Cl3IrNO

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; under 760.051 Torr; for 12h;	93%

chloroquinaldol (72-80-0) + 5-acetoxy-2-nitro-benzaldehyde (76143-12-9) → (E)-2-(5-acetoxy-2-nitrostyryl)-5,7-dichloroquinolin-8-yl acetate

Conditions	Yield
at 150℃;	92%

chloroquinaldol (72-80-0) + acetic anhydride (108-24-7) → 8-acetoxy-5,7-dichloro-2-methylquinoline (27039-48-1)

Conditions	Yield
With pyridine at 0 - 20℃; for 6h;	91%

chloroquinaldol (72-80-0) → 8-hydroxy-5,7-dichloro-2-(d3)methylquinoline

Conditions	Yield
With water-d2; benzoic acid at 120℃; for 4h;	91%
With water-d2; benzoic acid at 120℃; for 16h; Inert atmosphere; Schlenk technique;

chloroquinaldol (72-80-0) + 2-nitro-benzaldehyde (552-89-6) → (E)-5,7-dichloro-2-(2-nitrostyryl)quinolin-8-yl acetate

Conditions	Yield
at 150℃;	91%

chloroquinaldol (72-80-0) + benzyl bromide (100-39-0) → 8-(benzyloxy)-5,7-dichloro-2-methylquinoline (24010-00-2)

Conditions	Yield
With potassium carbonate In acetone for 5h; Reflux;	91%

chloroquinaldol (72-80-0) + 2,4-dinitrobenzaldehyde (528-75-6) + acetic anhydride (108-24-7) → 5,7-dichloro-2-[2-(2,4-dinitrophenyl)vinyl]quinolin-8-yl acetate

Conditions	Yield
With acetic acid at 130℃; Inert atmosphere;	91%

4,7-dichloro-1,10-phenanthroline (5394-23-0) + chloroquinaldol (72-80-0) + cobalt(II) salt → C32H18Cl6CoN4O2

Conditions	Yield
In methanol; acetonitrile at 80℃; for 24h;	90.8%

chloroquinaldol (72-80-0) + dipyrazine[2,3-f:2’,3’-h]quinoxaline (217-90-3) + cobalt(II) salt → C34H20Cl4CoN6O2

Conditions	Yield
In methanol; acetonitrile at 80℃; for 24h;	90.5%

[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + chloroquinaldol (72-80-0) → C32H22Cl2IrN3O

Conditions	Yield
In ethanol; water at 70℃; for 12h; Solvent; Temperature;	90.21%

sodium tetrafluoroborate (13755-29-8) + [RuCl2(hexamethylbenzene)]2 + chloroquinaldol (72-80-0) → [(η6-hexamethylbenzene)Ru(η2-N,O-5,7-dichloro-2-methyl-8-hydroxyquinolate)(H2O)]BF4 (1202404-57-6)

Conditions	Yield
With Ag2SO4 In water under inert atm.; mixt. of ((C6(CH3)6)RuCl2)2 (0.082 mmol) and Ag2SO4 (0.163 mmol) in H2O stirred for 2 h in dark at room temp., soln. filtered,NC9H3Cl2MeOH (0.163 mmol) added, stirred for 2 h in dark at room temp., pptd. by satd. aq. soln. of NaBF4; crystd. from H2O; elem. anal.;	90%

chloroquinaldol (72-80-0) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (5,7-dichloro-2-methylquinolin-8-yl)carbonate

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;	90%
With dmap; triethylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;	90%

dipyridil[3,2-a:2',3'-c]phenazine (19535-47-8) + chloroquinaldol (72-80-0) + cobalt(II) salt → C38H22Cl4CoN6O2

Conditions	Yield
In methanol; acetonitrile at 80℃; for 24h;	89.2%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + chloroquinaldol (72-80-0) + ytterbium(III) nitrate hexahydrate → [Yb(4,4'-dimethyl-2,2'-bipyridyl)(ClQ)2NO3]

Conditions	Yield
at 80℃; for 72h;	89.11%

chloroquinaldol (72-80-0) + 2,4-dichloro-6-formylphenyl acetate (1309272-63-6) + acetic anhydride (108-24-7) → 5,7-dichloro-2-[2-(2-acetoxy-3,5-dichlorophenyl)vinyl]quinolin-8-yl acetate

Conditions	Yield
With acetic acid at 130℃; Inert atmosphere;	88%

chloroquinaldol (72-80-0) + salicylaldehyde (90-02-8) → 5,7-dichloro-2-[2-(2-hydroxyphenyl)vinyl]quinolin-8-ol (1415220-29-9)

Conditions	Yield
Stage #1: chloroquinaldol; salicylaldehyde With acetic anhydride for 24h; Reflux; Stage #2: With pyridine In water for 3h; Reflux;	87%

chloroquinaldol (72-80-0) + trimethyl gallium (1445-79-0) → (5,7-dichloro-2-methyl-8-quinolinolato)dimethyl gallium

Conditions	Yield
In toluene at 24.84℃; for 16h; Inert atmosphere;	87%

chloroquinaldol (72-80-0) → 5,7-dichloro-8-hydroxy-2-methylquinoline 1-oxide (63504-03-0)

Conditions	Yield
With phosphoric acid; dihydrogen peroxide; molybdenum(VI) oxide In water; acetonitrile at 50℃;	87%

chloroquinaldol (72-80-0) + 5-fluoro-2-nitrobenzaldehyde (395-81-3) → (E)-5,7-dichloro-2-(5-fluoro-2-nitrostyryl)quinolin-8-yl acetate

Conditions	Yield
at 150℃;	87%

chloroquinaldol (72-80-0) + 2-nitroveratraldehyde (20357-25-9) → (E)-5,7-dichloro-2-(4,5-dimethoxy-2-nitrostyryl)quinolin-8-yl acetate

Conditions	Yield
at 150℃;	87%

Upstream product

• 826-81-3 2-methyl-8-quinolinol 
• 4369-36-2 dichlorohydantoin 
• 118-52-5 1,3-dichloro-5,5-dimethylhydantoin 
• 507-40-4 tert-butylhypochlorite 
• 21168-33-2 5,7-dichloro-8-hydroxyquinoline 1-oxide 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 1251918-08-7 5,7-dichloro-2-[2-(3,5-dihydroxyphenyl)vinyl]quinolin-8-ol 
• 1415220-30-2 5,7-dichloro-2-[2-(4-hydroxyphenyl)vinyl]quinolin-8-ol 
• 1415220-29-9 5,7-dichloro-2-[2-(2-hydroxyphenyl)vinyl]quinolin-8-ol 
• 1251918-07-6 5,7-dichloro-2-[2-(2,4-dihydroxyphenyl)vinyl]quinolin-8-ol 
• 1227180-25-7 5,7-dichloro-2-methylquinolin-8-yl tert-butyl(phenyl)posphinate 
• 1415222-54-6 C₃₅H₂₄Cl₅NO₂PRe 
• 1415222-58-0 C₃₅H₂₄Br₂Cl₃NO₂PRe 
• 796860-41-8 5,7-dichloro-2-[2-(2-chlorophenyl)vinyl]quinoline-8-ol 
• 1416988-91-4 C₂₂H₂₃Cl₃N₂O 
• 24010-00-2 8-(benzyloxy)-5,7-dichloro-2-methylquinoline 

Relevant articles and documents

Preparation method of chlorquinaldol

The invention provides a preparation method of chloroquinaldoll. The preparation method comprises the following step: in the presence of a catalyst Lewis acid, carrying out a reaction I on a material containing 8-hydroxy-2-methylquinoline and tert-butyl hypochlorite to obtain the chloroquinaldol. According to the method, the tert-butyl hypochlorite is used for replacing chlorine to serve as a reaction raw material, so good selectivity is achieved, byproducts are few, reaction operability is strong, light shielding and gas protection are not needed, quality and yield are improved, the purity of chlorquinaldol is 99.00% or more, and the quality of chlorquinaldol is ensured. In the reaction process, generation of waste liquid is reduced, pollution to the environment is avoided to the maximum extent, cost is saved, quality is improved, and the method is an environment-friendly process suitable for industrial production.

Preparation method of chloroquinaldol

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of chloroquinaldol. The preparation method comprises the following steps: adding water intochloroquinaldol hydrochloride for dissolving, adding a buffer solution under the conditions of light shielding and nitrogen protection, regulating the pH value by using alkali, filtering and refiningthe solution to obtain chloroquinaldol. The method is easy and convenient to operate and suitable for industrial production, the purity of the prepared chloroquinaldol is high and can reach 99.99% orabove, and the stability of the product is high.

Synthetic technology of chlorquinaldol

The invention belongs to the field of pharmaceutical synthesis technology and specifically relates to a synthetic technology of chlorquinaldol. By using Lewis acid as a catalyst, 8-hydroxy-2-methylquinoline and N-Chlorosuccinimide, which are used as raw materials, are subjected to a one-step chlorination reaction to generate chlorquinaldol; and after the reaction, chlorquinaldol is refined to obtain the chlorquinaldol. By using N-Chlorosuccinimide to replace chlorine as the raw material of the chlorination reaction, the selectivity is good, side reaction is reduced, conversion rate and yield are increased, yield reaches 98.2% and above, purity is 99.90% and above, quality of the chlorquinaldol is guaranteed, generation of spend liquor is decreased, environmental pollution is reduced, the cost is saved, water dissolution of the reaction product is avoided, and the yield is increased. The technology of the invention is a green and environmentally-friendly technology, and is suitable forindustrial production.