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144918-96-7

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144918-96-7 Usage

General Description

2,8-dichloro-quinoline-3-carbaldehyde is a chemical compound with a molecular formula C11H6Cl2NO. It is a yellow-colored solid substance with a strong odor that is commonly used as a building block in the synthesis of various organic compounds. This chemical is often utilized in research and industry for its ability to react with other compounds to form new chemical entities. Additionally, it is known to have potential applications in pharmaceuticals, agrochemicals, and materials science. As a result, 2,8-dichloro-quinoline-3-carbaldehyde is a valuable and versatile chemical with a wide range of potential uses in various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 144918-96-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,4,9,1 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 144918-96:
(8*1)+(7*4)+(6*4)+(5*9)+(4*1)+(3*8)+(2*9)+(1*6)=157
157 % 10 = 7
So 144918-96-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H5Cl2NO/c11-8-3-1-2-6-4-7(5-14)10(12)13-9(6)8/h1-5H

144918-96-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,8-Dichloroquinoline-3-carbaldehyde

1.2 Other means of identification

Product number -
Other names 2,8-dichloroquinoline-3-carboxaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:144918-96-7 SDS

144918-96-7Synthetic route

N-(2-chlorophenyl)acetamide
533-17-5

N-(2-chlorophenyl)acetamide

(4,6-dichloro-[1,3,5]triazin-2-yloxymethylene)-dimethyl-ammonium; chloride

(4,6-dichloro-[1,3,5]triazin-2-yloxymethylene)-dimethyl-ammonium; chloride

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

Conditions
ConditionsYield
In dichloromethane for 7h; Reflux;92%
N-(2-chlorophenyl)acetamide
533-17-5

N-(2-chlorophenyl)acetamide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

Conditions
ConditionsYield
With Triton X-100; trichlorophosphate In acetonitrile for 1.41667h; Vilsmeier-Haack cyclisation; Heating;88%
With trichlorophosphate at 80 - 100℃;
formic acid ethyl ester
109-94-4

formic acid ethyl ester

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 3h;
Stage #2: formic acid ethyl ester In tetrahydrofuran; hexane at -78℃; for 1h;
2,8-dichloroquinoline
4470-83-1

2,8-dichloroquinoline

formic acid ethyl ester
109-94-4

formic acid ethyl ester

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline With lithium diisopropyl amide In tetrahydrofuran; cyclohexene at -78℃; for 2h;
Stage #2: formic acid ethyl ester In tetrahydrofuran; cyclohexene at -78℃; for 4h;
2-Chloroaniline
95-51-2

2-Chloroaniline

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water
2: trichlorophosphate / 80 - 100 °C
View Scheme
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

2,8-dichloroquinoline
4470-83-1

2,8-dichloroquinoline

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In 2-methyltetrahydrofuran; hexane at -78 - -70℃;
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

(2-pyrazinyl)tributyltin

(2-pyrazinyl)tributyltin

8-chloro-2-(pyrazin-2-yl)quinoline-3-carbaldehyde
1362850-94-9

8-chloro-2-(pyrazin-2-yl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 110℃; for 5h; Inert atmosphere;99%
(R)-2-methylpropane-2-sulfinamide
196929-78-9

(R)-2-methylpropane-2-sulfinamide

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

(R,E)-N-[(2, 8-dichloroquinolin-3-yl)methylidene]-2-methylpropane-2-sulfinamide
1240186-26-8

(R,E)-N-[(2, 8-dichloroquinolin-3-yl)methylidene]-2-methylpropane-2-sulfinamide

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: (R)-2-methylpropane-2-sulfinamide at 20℃; for 17h;
97%
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: (R)-2-methylpropane-2-sulfinamide In tetrahydrofuran at 20℃; for 17h;
97%
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: (R)-2-methylpropane-2-sulfinamide In tetrahydrofuran at 20℃; for 17h;
97%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

8-chloro-2-phenylquinoline-3-carbaldehyde
1362850-80-3

8-chloro-2-phenylquinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 110℃; for 4h; Suzuki Coupling; Inert atmosphere;97%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

(S)-2-methylpropane-2-sulfinamide
343338-28-3

(S)-2-methylpropane-2-sulfinamide

2-methylpropane-2(S)-sulfinic acid N-(2,8-dichloroquinolin-3-yl)meth-(E)-ylideneamide
1362850-84-7

2-methylpropane-2(S)-sulfinic acid N-(2,8-dichloroquinolin-3-yl)meth-(E)-ylideneamide

Conditions
ConditionsYield
Stage #1: (S)-2-methylpropane-2-sulfinamide With potassium phosphate In water for 0.166667h;
Stage #2: 2,8-dichloroquinoline-3-carbaldehyde In water; isopropyl alcohol for 48h;
95%
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(pyridin-3-yl)quinoline-3-carbaldehyde
1362850-73-4

8-chloro-2-(pyridin-3-yl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 7h; Suzuki Coupling; Inert atmosphere;91%
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tri tert-butylphosphoniumtetrafluoroborate In ethanol; water at 70℃; Inert atmosphere;
(R)-2-methylpropane-2-sulfinamide
196929-78-9

(R)-2-methylpropane-2-sulfinamide

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

N-[(2,8-dichloroquinolin-3-yl)methylene]-2-methylpropane-2(R)-sulfinamide
1256280-05-3

N-[(2,8-dichloroquinolin-3-yl)methylene]-2-methylpropane-2(R)-sulfinamide

Conditions
ConditionsYield
titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 17.25h; Inert atmosphere;89%
4,6-dihydroxy-2-mercaptopyrimidine
504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

Chloroacetic anhydride
541-88-8

Chloroacetic anhydride

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

C22H13Cl4N3O8S

C22H13Cl4N3O8S

Conditions
ConditionsYield
With copper In ethanol for 1h; Irradiation;89%
2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine
1012084-56-8

2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(2-methylpyridin-3-yl)quinoline-3-carbaldehyde
1065481-93-7

8-chloro-2-(2-methylpyridin-3-yl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃; for 3h;86.43%
o-fluorophenylboronic acid
1993-03-9

o-fluorophenylboronic acid

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(2-fluorophenyl)quinoline-3-carbaldehyde
1065481-78-8

8-chloro-2-(2-fluorophenyl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃; for 1h;83.1%
4-cyclohexyl-thiosemicarbazide
21198-18-5

4-cyclohexyl-thiosemicarbazide

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

1-((2,8-dichloroquinolin-3-yl)methylene)-4-cyclohexylthiosemicarbazide
1313027-61-0

1-((2,8-dichloroquinolin-3-yl)methylene)-4-cyclohexylthiosemicarbazide

Conditions
ConditionsYield
Stage #1: 4-cyclohexyl-thiosemicarbazide; 2,8-dichloroquinoline-3-carbaldehyde In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
81%
thiosemicarbazide
79-19-6

thiosemicarbazide

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

1-((2,8-dichloroquinolin-3-yl)methylene)thiosemicarbazide
1313027-60-9

1-((2,8-dichloroquinolin-3-yl)methylene)thiosemicarbazide

Conditions
ConditionsYield
Stage #1: thiosemicarbazide; 2,8-dichloroquinoline-3-carbaldehyde In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
79%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

4-(4-methylphenyl)-3-thiosemicarbazide
13278-67-6

4-(4-methylphenyl)-3-thiosemicarbazide

1-((2,8-dichloroquinolin-3-yl)methylene)-4-p-tolylthiosemicarbazide
1313027-63-2

1-((2,8-dichloroquinolin-3-yl)methylene)-4-p-tolylthiosemicarbazide

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde; 4-(4-methylphenyl)-3-thiosemicarbazide In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
76%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

4-cyclopentyl thiosemicarbazide
122813-74-5

4-cyclopentyl thiosemicarbazide

1-((2,8-dichloroquinolin-3-yl)methylene)-4-cyclopentylthiosemicarbazide
1313027-64-3

1-((2,8-dichloroquinolin-3-yl)methylene)-4-cyclopentylthiosemicarbazide

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde; 4-cyclopentyl thiosemicarbazide In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
76%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

2-trifluoromethoxyphenylboronic acid
175676-65-0

2-trifluoromethoxyphenylboronic acid

8-chloro-2-(2-(trifluoromethoxy)phenyl)quinoline-3-carbaldehyde
1065481-61-9

8-chloro-2-(2-(trifluoromethoxy)phenyl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃; for 15h;70.9%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

6-chloropyridin-3-ylboronic acid
444120-91-6

6-chloropyridin-3-ylboronic acid

8-chloro-2-(6-chloropyridin-3-yl)quinoline-3-carbaldehyde
1362851-52-2

8-chloro-2-(6-chloropyridin-3-yl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 16h; Suzuki Coupling; Inert atmosphere;70%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

4-(2-methylphenyl)-3-thiosemicarbazide
614-10-8

4-(2-methylphenyl)-3-thiosemicarbazide

1-((2,8-dichloroquinolin-3-yl)methylene)-4-o-tolylthiosemicarbazide
1313027-62-1

1-((2,8-dichloroquinolin-3-yl)methylene)-4-o-tolylthiosemicarbazide

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde; 4-(2-methylphenyl)-3-thiosemicarbazide In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
69%
4-(4-nitrophenyl)-3-thiosemicarbazide
38985-70-5

4-(4-nitrophenyl)-3-thiosemicarbazide

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

1-((2,8-dichloroquinolin-3-yl)methylene)-4-p-nitrophenylthiosemicarbazide
1313027-73-4

1-((2,8-dichloroquinolin-3-yl)methylene)-4-p-nitrophenylthiosemicarbazide

Conditions
ConditionsYield
Stage #1: 4-(4-nitrophenyl)-3-thiosemicarbazide; 2,8-dichloroquinoline-3-carbaldehyde In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
67%
2-methoxy-6-(tri-n-butylstannyl)pyrazine
1105511-66-7

2-methoxy-6-(tri-n-butylstannyl)pyrazine

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(6-methoxypyrazin-2-yl)quinoline-3-carbaldehyde
1362850-98-3

8-chloro-2-(6-methoxypyrazin-2-yl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 110℃; Inert atmosphere;63%
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

C8H15NHCSNHNH2
122813-76-7

C8H15NHCSNHNH2

1-((2,8-dichloroquinolin-3-yl)methylene)-4-cyclooctylthiosemicarbazide
1313027-67-6

1-((2,8-dichloroquinolin-3-yl)methylene)-4-cyclooctylthiosemicarbazide

Conditions
ConditionsYield
Stage #1: 2,8-dichloroquinoline-3-carbaldehyde; C8H15NHCSNHNH2 In ethanol
Stage #2: With acetic acid In ethanol at 60℃; for 12h;
62%
(5-fluoro-2-(trifluoromethyl)phenyl)boronic acid
928053-97-8

(5-fluoro-2-(trifluoromethyl)phenyl)boronic acid

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(5-fluoro-2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde
1065481-66-4

8-chloro-2-(5-fluoro-2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃; for 14h;19.4%
2-(trifluoromethyl)phenylboronic acid
1423-27-4

2-(trifluoromethyl)phenylboronic acid

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde
1064136-74-8

8-chloro-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃;
(5-fluoro-2-methoxyphenyl)boronic acid
179897-94-0

(5-fluoro-2-methoxyphenyl)boronic acid

2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-carbaldehyde
1065481-40-4

8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃; for 4h;
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

(S)-tert-butyl 1-(2,8-dichloroquinolin-3-yl)ethylcarbarnate
1240186-30-4

(S)-tert-butyl 1-(2,8-dichloroquinolin-3-yl)ethylcarbarnate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: Cooling with ice
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: titanium(IV)isopropoxide / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 17 h / 20 °C / Inert atmosphere
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: cooling with ice-salt
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
View Scheme
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

(R)-N-[(S)-1-(2,8-dichloroquinolin-3-yl)ethyl]-2-methylpropane-2-sulfinamide
1240186-28-0

(R)-N-[(S)-1-(2,8-dichloroquinolin-3-yl)ethyl]-2-methylpropane-2-sulfinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: titanium(IV)isopropoxide / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 17 h / 20 °C / Inert atmosphere
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: cooling with ice-salt
View Scheme
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

(S)-1-(2,8-dichloroquinolin-3-yl)ethanamine
1240186-29-1

(S)-1-(2,8-dichloroquinolin-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: Cooling with ice
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: titanium(IV)isopropoxide / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h
View Scheme
Multi-step reaction with 3 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 17 h / 20 °C / Inert atmosphere
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: cooling with ice-salt
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C / Inert atmosphere
View Scheme
2,8-dichloroquinoline-3-carbaldehyde
144918-96-7

2,8-dichloroquinoline-3-carbaldehyde

C23H32ClN5O3
1242181-15-2

C23H32ClN5O3

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 20 °C
1.2: 17 h / 20 °C
2.1: dichloromethane; diethyl ether / -70 - 20 °C / Inert atmosphere
2.2: Cooling with ice
3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 130 °C / microwave irradiation
View Scheme

144918-96-7Relevant articles and documents

2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier-Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides

Venkanna,Rajanna,Satish Kumar,Bismillah Ansari, Mohd.,Moazzam Ali

, p. 5164 - 5167 (2015)

TCTA-DMF (2,4,6-trichloro-1,3,5-triazine/N,N′-dimethylformamide) adduct has been used as a Vilsmeier-Haack type reagent for effective synthesis of 2-chloro-3-formyl quinolines from acetanilides under conventional and ultrasonically assisted conditions. The reaction times under sonication are quite significantly shorter than conventional methods even though the yields obtained under sonication are comparable with those obtained under reflux conditions.

CRYSTALLINE FORMS OF SELETALISIB

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Page/Page column 9, (2019/01/04)

Crystalline forms of seletalisib, designated as Form B and Form F and characterized herein, being selective inhibitors of PI3 kinase enzymes, in particular of the human ΡΒΚδ isoform, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

TRISUBSTITUTED AMINE COMPOUND

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Page/Page column 142-143, (2008/06/13)

The present invention relates to a compound of the general formula (1): wherein, Y is a methylene group, and the like; A is an optionally substituted heterocyclic group, and the like; B is an optionally substituted heterocyclic group, and the like; R1 is an optionally substituted alkyl group, wherein the alkyl group further may optionally be substituted by an optionally substituted homocyclic group, and the like; and R2 is an optionally substituted amino group, and the like; or a pharmaceutically acceptable derivative thereof, which has an inhibitory activity against cholesteryl ester transfer protein (CETP), thereby being useful for prophylaxis and/or treatment of arteriosclerotic diseases, hyperlipemia or dyslipidemia, and the like.

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