86-98-6

Basic information

• Product Name: 4,7-Dichloroquinoline
• Synonyms: 4,7-dichloro-quinolin;TL 1473;tl1473;4,7-DICHLOROQUINOLINE;4,7-DICHLOROQUINOLINE, 99+%;4,7-Dichloroquinoline,97%;4,7-DICHLOLROQUINOLINE;4,7-DICHLOROQUINOLINE CHLOROQUINE PHOSPHATE
• CAS NO: 86-98-6
• Molecular Formula: C₉H₅Cl₂N
• Molecular Weight: 198.05
• EINECS: 201-714-7
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Quinolines;Haloquinolines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;QuinolinesHeterocyclic Building Blocks;Building Blocks;C8 to C10;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 86-98-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 148 °C
• Flash Point: 164 °C
• Appearance: White to pale brown/Powder
• Density: 1.4178 (rough estimate)
• Vapor Pressure: 0.00313mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: chloroform: soluble50mg/mL, clear, colorless to greenish-yellow
• PKA: 1.99±0.27(Predicted)
• Water Solubility: insoluble
• BRN: 125359
• CAS DataBase Reference: 4,7-Dichloroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-Dichloroquinoline(86-98-6)
• EPA Substance Registry System: 4,7-Dichloroquinoline(86-98-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-22
• WGK Germany: 3
• RTECS: VB4200000
• TSCA: Yes
• Hazardous Substances Data: 86-98-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 86-98-6 differently. You can refer to the following data:
1. 4,7-Dichloroquinoline is used in the synthesis of hybrid aminoquinoline-triazine derivatives that show anti-microbial activity. In addition, it is used in the synthesis of novel oxazolidinones as anti -microbial agents showing efficacy against common bacterial strains. Chloroquinoline impurity.
2. 4,7-Dichloroquinoline is used as a drug chloroquine phosphate intermediate. It is also is used in the synthesis of hybrid aminoquinoline-triazine derivatives that show anti-microbial activity. In addition, it is used in the synthesis of novel oxazolidinones as anti-microbial agents showing efficacy against common bacterial strains.
3. 4,7-Dichloroquinoline was used in the synthesis of piperaquine. It was used as starting reagent in the synthesis of {3-amino-5-[(7-chloro-4-quinolyl)amino]phenyl}methanol.

General Description

Chloroquine Related Compound A is an impurity of chloroquine, which is a 9-aminoquinoline drug that effectively inhibits viral infections in humans.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the dichloroquinoline from MeOH or 95% EtOH. [Beilstein 20/7 V 316.]

InChI:InChI=1/C9H5Cl2N/c10-6-1-2-7-8(11)3-4-12-9(7)5-6/h1-5H

Synthetic route

7-chloro-4-hydroxylquinoline (86-99-7) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
With trichlorophosphate for 1h; Heating;	94%
With trichlorophosphate Reflux;	89.5%
With trichlorophosphate for 2h; Heating / reflux;	88.5%

7-chloro-4(1H)-oxoquinoline (23833-97-8) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
With trichlorophosphate for 2h; Reflux;	85%
With trichlorophosphate for 2h; Reflux;	85%
With ((1,3,5-triazine-2,4,6-triyl)tris(oxy))tris(triphenylphosphonium) chloride at 140 - 150℃; for 2h; Solvent; Ionic liquid;
With trichlorophosphate Reflux;

7-fluoro-1,4-dihydroquinolin-4-one (391-83-3, 183057-60-5) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
With trichlorophosphate for 1h; Reflux;	85%

4,7-dichloroquinoline 1-oxide (1077-74-3) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
With Eosin Y; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 1h; Inert atmosphere; Irradiation; chemoselective reaction;	78%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Irradiation; chemoselective reaction;	73%

4,7-dichloro-1,2,3,4-tetrahydroquinoline → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In n-heptane at 100℃; under 11251.1 Torr; for 12h; Autoclave;	62%

7-chloro-4-quinolinesulfonyl chloride (1134937-73-7) → 4,7-dichloroquinoline (86-98-6) + 7-chloro-4-quinolinesulfonamide (1134937-74-8)

Conditions	Yield
With ammonia In water at 20℃;	A 31% B 56%

5-[(3-chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (25063-49-4) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenyl ether / 0.08 h / 300 °C / microwave irradiation 2: POCl3 / 3 h / Heating View Scheme

2-acetyl-5-chloroaniline (39061-72-8) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: 75 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 95 percent / K2CO3 / dimethylformamide / 1 h / 80 °C 3: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 4: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 5: 81 percent / aq. NaOH / methanol / Heating 6: 94 percent / POCl3 / 1 h / Heating View Scheme

N-(2-acetyl-5-chlorophenyl)-4-methylbenzenesulfonamide (675578-62-8) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / K2CO3 / dimethylformamide / 1 h / 80 °C 2: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 3: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 4: 81 percent / aq. NaOH / methanol / Heating 5: 94 percent / POCl3 / 1 h / Heating View Scheme

N-allyl-N-p-toluenesulfonyl-2-acetyl-5-chloroaniline (675578-63-9) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 2: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 3: 81 percent / aq. NaOH / methanol / Heating 4: 94 percent / POCl3 / 1 h / Heating View Scheme

N-p-toluenesulfonyl-4-(t-butyldimethylsilyloxy)-7-chloro-1,2-dihydroquinoline (675578-65-1) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / aq. NaOH / methanol / Heating 2: 94 percent / POCl3 / 1 h / Heating View Scheme

N-allyl-N-p-toluenesulfonyl-2-[1-(tert-butyldimethylsilyloxy)vinyl]-5-chloroaniline (675578-64-0) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 2: 81 percent / aq. NaOH / methanol / Heating 3: 94 percent / POCl3 / 1 h / Heating View Scheme

4-hydroxy-7-chloro-3-quinoline-carboxylic acid (86-47-5) → 4,7-dichloroquinoline (86-98-6) + N,Ndiethyl-butanediyldiamine

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenyl ether / 1 h / Heating 2: POCl3 / 100 °C View Scheme

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester (16600-22-9) → 4,7-dichloroquinoline (86-98-6) + N,Ndiethyl-butanediyldiamine

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 N aq. NaOH / 1 h / Heating 2: diphenyl ether / 1 h / Heating 3: POCl3 / 100 °C View Scheme

2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5) → 4,7-dichloroquinoline (86-98-6) + N,Ndiethyl-butanediyldiamine

Conditions	Yield
Multi-step reaction with 4 steps 1: diphenyl ether / 1 h / Heating 2: 2 N aq. NaOH / 1 h / Heating 3: diphenyl ether / 1 h / Heating 4: POCl3 / 100 °C View Scheme

3-chloro-aniline (108-42-9) + potassium-<6-chloro-3-nitro benzoate> → 4,7-dichloroquinoline (86-98-6) + N,Ndiethyl-butanediyldiamine

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.5 h / 165 °C 2: diphenyl ether / 1 h / Heating 3: 2 N aq. NaOH / 1 h / Heating 4: diphenyl ether / 1 h / Heating 5: POCl3 / 100 °C View Scheme

4-hydroxy-7-chloro-3-quinoline-carboxylic acid (86-47-5) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 2: phosphoryl chloride View Scheme

7-chlorokynurenic acid (18000-24-3) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: mineral oil / 270 °C 2: phosphoryl chloride View Scheme
Multi-step reaction with 2 steps 1: 1-chloro-naphthalene 2: phosphoryl chloride View Scheme

7-chloro-4-hydroxy-quinoline-2-carboxylic acid ethyl ester (21640-97-1) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous NaOH 2: mineral oil / 270 °C 3: phosphoryl chloride View Scheme
Multi-step reaction with 3 steps 1: aqueous NaOH 2: 1-chloro-naphthalene 3: phosphoryl chloride View Scheme

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester (16600-22-9) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous NaOH 2: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 3: phosphoryl chloride View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide; water / diphenylether / 0.5 h 2: paraffin oil / 0.83 h / 230 °C 3: trichlorophosphate / Reflux View Scheme

2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 4 steps 2: aqueous NaOH 3: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 4: phosphoryl chloride View Scheme
Multi-step reaction with 2 steps 1: dowtherm / 4 h 2: trichlorophosphate / 6 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: diphenylether / Reflux 2: sodium hydroxide; ethanol / Reflux 3: diphenylether / Reflux 4: trichlorophosphate / 2 h / Reflux View Scheme

3-chloro-aniline (108-42-9) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid / Erhitzen des Reaktionsprodukts in Paraffinoel auf 250grad 2: aqueous NaOH 3: mineral oil / 270 °C 4: phosphoryl chloride View Scheme
Multi-step reaction with 5 steps 3: aqueous NaOH 4: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 5: phosphoryl chloride View Scheme
Multi-step reaction with 4 steps 1: acetic acid / Erhitzen des Reaktionsprodukts in Paraffinoel auf 250grad 2: aqueous NaOH 3: mineral oil / 270 °C 4: phosphoryl chloride View Scheme

3-chloro-aniline (108-42-9) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Stage #1: 3-chloro-aniline; diethyl 2-ethoxymethylenemalonate Heating; Stage #2: With trichlorophosphate

7-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid ethyl ester (26892-97-7, 53977-12-1) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 1 h / Reflux 2: diphenylether / 0.5 h / Reflux 3: trichlorophosphate / 1 h / Reflux View Scheme

7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (183057-56-9, 63463-20-7) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenylether / 0.5 h / Reflux 2: trichlorophosphate / 1 h / Reflux View Scheme

meta-fluoroaniline (372-19-0) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 2 h / 100 °C 2: diphenylether / 0.25 h / Reflux 3: sodium hydroxide / 1 h / Reflux 4: diphenylether / 0.5 h / Reflux 5: trichlorophosphate / 1 h / Reflux View Scheme

C14H16FNO4 → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: diphenylether / 0.25 h / Reflux 2: sodium hydroxide / 1 h / Reflux 3: diphenylether / 0.5 h / Reflux 4: trichlorophosphate / 1 h / Reflux View Scheme

7-chloro-4(1H)-oxoquinoline-3-carboxylic acid → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenylether / Reflux 2: trichlorophosphate / 2 h / Reflux View Scheme

ethyl 7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (54132-35-3) → 4,7-dichloroquinoline (86-98-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; ethanol / Reflux 2: diphenylether / Reflux 3: trichlorophosphate / 2 h / Reflux View Scheme

4,7-dichloroquinoline (86-98-6) + heptane-1,7-diamine (646-19-5) → N-(7-chloro-[4]quinolyl)-heptanediyldiamine (102882-13-3)

Conditions	Yield
Inert atmosphere;	100%
In pentan-1-ol at 120℃; for 16h;	80%
With N-ethyl-N,N-diisopropylamine In pentan-1-ol for 18h; Heating;	80%

4,7-dichloroquinoline (86-98-6) + ethylenediamine (107-15-3) → N-(7-chloroquinolin-4-yl)ethylenediamine (5407-57-8)

Conditions	Yield
at 80 - 140℃; for 13h;	100%
at 80 - 135℃; for 4h; neat (no solvent);	100%
In neat (no solvent) at 110℃;	100%

4,7-dichloroquinoline (86-98-6) + 4-bromo-aniline (106-40-1) → N-(4-bromophenyl)-7-chloroquinolin-4-amine

Conditions	Yield
In ethanol for 24h; Reflux;	100%
for 0.166667h; microwave irradiation;	95%
With ethanol

piperazine (110-85-0) + 4,7-dichloroquinoline (86-98-6) → 7-chloro-4-piperazinylquinoline (837-52-5)

Conditions	Yield
In isopropyl alcohol at 100℃; for 20h;	100%
With triethylamine at 130℃; for 4h; Inert atmosphere;	98%
With potassium carbonate In isopropyl alcohol for 36h; Reflux;	95%

4,7-dichloroquinoline (86-98-6) + 1,8-diaminooctan (373-44-4) → N-(7-chloroquinolin-4-yl)octane-1,8-diamine (1025956-25-5)

Conditions	Yield
Inert atmosphere;	100%
at 80 - 140℃; for 2.75h; Microwave irradiation;	69%
at 80 - 135℃; for 4h;	51%

4,7-dichloroquinoline (86-98-6) + diaminodecane (646-25-3) → N-(7-chloroquinolin-4-yl)decane-1,10-diamine (1026600-71-4)

Conditions	Yield
Inert atmosphere;	100%
at 80 - 135℃; for 4h;	60%
1.) 80 deg C, 1 h, 2.) 135-145 deg C, 3 h;

4,7-dichloroquinoline (86-98-6) + 1,12-Diaminododecane (2783-17-7) → N1-(7-Chloro-quinolin-4-yl)-dodecane-1,12-diamine (1026678-59-0)

Conditions	Yield
Inert atmosphere;	100%
1.) 80 deg C, 1 h, 2.) 135-145 deg C, 3 h;

4,7-dichloroquinoline (86-98-6) + Trimethylenediamine (109-76-2) → N-(7-chloroquinolin-4-yl)propane-1,3-diamine (7597-14-0)

Conditions	Yield
In neat (no solvent) at 110℃;	100%
Inert atmosphere;	100%
In isopropyl alcohol at 100℃; for 20h;	98%

4,7-dichloroquinoline (86-98-6) + 1,4-diaminobutane (110-60-1) → N1-(7-chloroquinolin-4-yl)butane-1,4-diamine (53186-45-1)

Conditions	Yield
Inert atmosphere;	100%
at 95℃; for 1h; Microwave irradiation;	100%
In isopropyl alcohol at 100℃; for 20h;	99%

4,7-dichloroquinoline (86-98-6) + silver thiocyanate (1701-93-5) → 7-chloro-4-isothiocyanatoquinoline (884647-32-9)

Conditions	Yield
In toluene at 110℃; for 12h;	100%
In toluene at 115℃; for 18h;	89%
In toluene at 90 - 120℃; for 18h;	68%
In toluene for 12h; Heating;
In toluene at 120℃; for 18h;

4,7-dichloroquinoline (86-98-6) + propan-1-ol-3-amine (156-87-6) → 3-[(7-chloroquinolin-4-yl)amino]propan-1-ol (60548-22-3)

Conditions	Yield
Inert atmosphere;	100%
With triethylamine In ethanol at 90℃;	99%
With triethylamine In N,N-dimethyl-formamide at 60 - 120℃; for 24h;	96%

5-amino-4'-trifluoromethyl-biphenyl-3-ol (927408-15-9) + 4,7-dichloroquinoline (86-98-6) → 5-(7-chloro-quinolin-4-ylamino)-4'-trifluoromethyl-biphenyl-3-ol (927407-98-5)

Conditions	Yield
In ethanol for 2h; Heating;	100%

4,7-dichloroquinoline (86-98-6) + aniline (62-53-3) → (7-chloroquinolin-4-yl)-phenyl-amine (83674-18-4)

Conditions	Yield
In ethanol for 24h; Reflux;	100%
In neat (no solvent) at 120℃; under 1500.15 Torr; for 0.166667h; Microwave irradiation;	96%
for 0.116667h; microwave irradiation;	95%

4,7-dichloroquinoline (86-98-6) + 7-amino-3-ethylquinazolin-4(3H)-one (873850-11-4) → C19H15ClN4O (1414781-94-4)

Conditions	Yield
In ethanol for 48h; Reflux;	100%

4,7-dichloroquinoline (86-98-6) + 7-amino-3-propylquinazolin-4(3H)-one (1414782-02-7) → C20H17ClN4O (1414781-95-5)

Conditions	Yield
In ethanol for 48h; Reflux;	100%

4,7-dichloroquinoline (86-98-6) + 7-amino-3-benzylquinazolin-4(3H)-one (591755-15-6) → C24H17ClN4O (1414781-96-6)

Conditions	Yield
In ethanol for 48h; Reflux;	100%

4,7-dichloroquinoline (86-98-6) + 4-methoxy-aniline (104-94-9) → 7-chloro-N-(4-methoxyphenyl)quinolin-4-amine (6059-31-0)

Conditions	Yield
With trifluoroacetic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane for 8.53333h; Inert atmosphere; Reflux;	99%
With phenol at 120℃; for 0.5h;	98%
for 0.25h; microwave irradiation;	78%
With silica gel-loaded acidic ionic liquid IL/TFA at SiO2 In 1-methyl-pyrrolidin-2-one at 70℃;	36.8%
With hydrogenchloride

4,7-dichloroquinoline (86-98-6) + ethanolamine (141-43-5) → 3-(7-chloroquinolin-4-ylamino)propyl alcohol (91066-18-1)

Conditions	Yield
With triethylamine In ethanol at 90℃;	99%
at 130 - 140℃; for 24h;	97%
In neat (no solvent) at 130℃;	95%

4,7-dichloroquinoline (86-98-6) → 4-amino-7-chloroquinoline (1198-40-9)

Conditions	Yield
With ammonium carbonate; phenol at 110 - 165℃;	99%
With ammonia In phenol at 170℃; for 2h;	92%
With ammonia; phenol at 150℃; for 2h;	89%

4,7-dichloroquinoline (86-98-6) + 4-amino-phenol (123-30-8) → 4-((4-hydroxyphenyl)amino)-7-chloroquinolinium chloride

Conditions	Yield
In ethanol Reflux;	99%
With hydrogenchloride; potassium iodide In ethanol for 12h; Heating;

4,7-dichloroquinoline (86-98-6) + dimethyl amine (124-40-3) → 7-chloro-4-N,N-dimethylamino-quinoline (22072-07-7)

Conditions	Yield
In water; acetonitrile at 50℃; for 48h;	99%
In water; acetonitrile at 50℃; for 48h;	90%
With acetic acid at 130 - 135℃; for 3h;	40%

4,7-dichloroquinoline (86-98-6) + m-Hydroxyaniline (591-27-5) → 4-(3'-hydroxyphenyl)amino-7-chloroquinoline (154179-33-6)

Conditions	Yield
In ethanol Reflux;	99%
for 0.25h; microwave irradiation;	75%
With hydrogenchloride; potassium iodide In ethanol Heating;

1H-imidazole (288-32-4) + 4,7-dichloroquinoline (86-98-6) → 7-chloro-4-(1H-imidazol-1-yl)quinoline (54666-24-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry;	99%
for 0.0333333h; microwave irradiation;	85%

4,7-dichloroquinoline (86-98-6) + 1 ,5-pentanediol (111-29-5) → O-(7-chloro-4-quinolyl)-1,5-pentanediol (1033132-57-8)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h; Inert atmosphere;	99%

4,7-dichloroquinoline (86-98-6) + trimethyleneglycol (504-63-2) → O-(7-chloro-4-quinolyl)-1,3-propanediol (1033132-54-5)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h; Inert atmosphere;	99%
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h;

4,7-dichloroquinoline (86-98-6) + 5-amino-4'-chloro<1,1'-biphenyl>-2-ol (79287-36-8) → 4’-chloro-5-[(7-chloro-4-quinolinyl)amino]-[1,1’-biphenyl]-2-ol (1101170-94-8)

Conditions	Yield
With hydrogenchloride In ethanol; water for 10h; Reflux;	99%
With hydrogenchloride In ethanol; water for 4h; Inert atmosphere; Reflux;	87%

4,7-dichloroquinoline (86-98-6) + methyl trifluoromethanesulfonate (333-27-7) → 4,7-dichloro-1-methylquinolinium triflate (1255923-14-8)

Conditions	Yield
In dichloromethane at 20℃; for 18h;	99%
In toluene at 20℃; for 24h;	65%

4,7-dichloroquinoline (86-98-6) + 2-Fluoroaniline (348-54-9) → 7-chloro-4-[(2-fluorophenyl)amino]quinolinium chloride

Conditions	Yield
In ethanol Reflux;	99%

4,7-dichloroquinoline (86-98-6) + 2-Chloroaniline (95-51-2) → 7-chloro-4-[(2-chlorophenyl)amino]quinolinium chloride

Conditions	Yield
In ethanol Reflux;	99%

4,7-dichloroquinoline (86-98-6) + 4-bromo-aniline (106-40-1) → 4-[(4-bromophenyl)amino]-7-chloroquinolinium chloride

Conditions	Yield
In ethanol Reflux;	99%

Upstream product

• 675578-62-8 N-(2-acetyl-5-chlorophenyl)-4-methylbenzenesulfonamide 
• 675578-63-9 N-allyl-N-p-toluenesulfonyl-2-acetyl-5-chloroaniline 
• 86-99-7 7-chloro-4-hydroxylquinoline 
• 1077-74-3 4,7-dichloroquinoline 1-oxide 
• 372-19-0 meta-fluoroaniline 
• 391-83-3 7-fluoro-1,4-dihydroquinolin-4-one 
• 183057-56-9 7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 26892-97-7 7-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid ethyl ester 
• 108-42-9 3-chloro-aniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 23833-97-8 7-chloro-4(1H)-oxoquinoline 
• 1134937-73-7 7-chloro-4-quinolinesulfonyl chloride 
• 3412-99-5 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester 
• 16600-22-9 7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester 

Downstream Products

• 26707-52-8 7-chloro-4-methoxyquinoline 
• 24616-89-5 7-chloro-N-<3-(diethylamino)methyl-4-methoxyphenyl>-4-quinolamine 
• 5418-53-1 2-[3-(7-chloro-[4]quinolylamino)-propylamino]-ethanol 
• 132400-21-6 4-(7-chloro-quinolin-4-ylamino)-2-(morpholin-4-ylmethyl)phenol 
• 5418-56-4 NCI0010488 
• 5418-58-6 N-butyl-N'-(7-chloro-[4]quinolyl)-N-(2-hydroxy-ethyl)-propanediyldiamine 
• 7597-14-0 N-(7-chloroquinolin-4-yl)propane-1,3-diamine 
• 47292-84-2 N,N-diethyl-N'-(7-chloro-[4]quinolyl)-cyclohexane-1,3-diyldiamine 
• 83196-67-2 7-chloro-N-<3-(diethylamino)methylphenyl>-4-quinolinamine 
• 874498-25-6 4,7-dichloro-2-(4-chlorophenyl)quinoline 
• 101726-93-6 4,7-dichloro-2-(4-methoxy-phenyl)-quinoline 
• 5448-52-2 7-chloro-4-ethoxyquinoline 
• 161467-72-7 7-chloro-4-(p-tolylthio)quinoline 

Relevant articles and documents

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Synthesis method of 4,7-dichloroquinoline

The invention discloses a synthesis method of 4,7-dichloroquinoline. The synthesis method is characterized by comprising the following steps: synthesizing 7-chloro-4-hydroxylquinoline-3-carboxylic acid by using a one-pot method, and carrying out decarboxylation and chlorination on the 7-chloro-4-hydroxylquinoline-3-carboxylic acid to obtain 4,7-dichloroquinoline. The step of synthesizing the 7-chloro-4-hydroxylquinoline-3-carboxylic acid by the one-pot method comprises the following sub-steps: with m-chloroaniline, triethyl orthoformate or trimethyl orthoformate and diethyl malonate as raw materials, carrying out condensation under the catalysis of anhydrous ferric trichloride to obtain diethyl 2-[[(3-chlorophenyl)amino]methylene]malonate, directly adding a condensation reaction solution into an organic solvent, carrying out heating cyclization to obtain 7-chloro-4-hydroxylquinoline-3-carboxylic acid ethyl ester, and after the cyclization reaction is completed, adding sodium hydroxidefor hydrolysis to obtain 7-chloro-4-hydroxylquinoline-3-carboxylic acid. Although the whole process comprises five reactions, intermediate products are good enough in purity and can be directly synthesized into a target product without purification, so operation is easy and convenient and industrialization is facilitated; and raw materials are easily available, and pollution is small.