3-Quinolinecarboxaldehyde,2-chloro-7-methoxy- supplier

Name
2-CHLORO-7-METHOXY-QUINOLINE-3-CARBALDEHYDE
EINECS
CAS No. 68236-20-4
Article Data52
CAS DataBase
Density 1.348 g/cm³
Solubility
Melting Point 196-198 ºC
Formula C₁₁H₈ClNO₂
Boiling Point 373.9 °C at 760 mmHg
Molecular Weight 221.643
Flash Point 179.9 °C
Transport Information
Appearance
Safety 26
Risk Codes 36-22
Molecular Structure
Hazard Symbols Xn
Synonyms 2-Chloro-3-formyl-7-methoxyquinoline;2-Chloro-7-methoxy-3-quinolinecarboxaldehyde;7-Methoxy-2-chloro-3-formylquinoline;
PSA 39.19000
LogP 2.70930

Synthetic route

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

: 588-16-9
m-methoxyacetanilide

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
With trichlorophosphate for 4h; Heating;	89%
With trichlorophosphate at 80 - 90℃; for 4h; Vilsmeier-Haack cyclisation;	89%
With trichlorophosphate at 80 - 90℃;	89%

: 101382-55-2
7-methoxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehyde

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
With trichlorophosphate Heating;

: 536-90-3
m-Anisidine

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O 2: 89 percent / POCl3 / 80 - 90 °C View Scheme
Multi-step reaction with 2 steps 1: H2O 2: 89 percent / POCl3 / 4 h / 80 - 90 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 25 °C 2: trichlorophosphate / 16 h / 0 - 80 °C View Scheme

: 51-66-1
4-methoxyacetanilide

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

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
With trichlorophosphate

: 90-04-0
2-methoxy-phenylamine

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C 2.1: trichlorophosphate / 0.08 h / 0 °C 2.2: Heating View Scheme

: 50868-75-2
5’-methoxy-2’-methylacetanilide

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

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; Stage #2: 5’-methoxy-2’-methylacetanilide at 80℃; for 14h;

: 50868-72-9
5-methoxy-o-toluidine

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid / 2.5 h / 20 - 80 °C 2.1: trichlorophosphate / 0 - 5 °C 2.2: 14 h / 80 °C View Scheme

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: (E)-2-chloro-3-(hydrazonomethyl)-7-methoxyquinoline

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol	100%
With hydrazine hydrate In ethanol at 20℃; for 18h;	80%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 627-41-8
propargyl alcohol methyl ether

: C15H13NO3

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; Sonogashira reaction;	100%
With copper(l) iodide; bis(tri-phenylphosphine)palladium(II) dichloride; triethylamine In N,N-dimethyl-formamide at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;	58%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: C19H17NOPPol

: 1287695-24-2
N-((E)-(2-chloro-6-methoxyquinolin-3-yl)methylidene)-4-methoxyaniline

Conditions

Conditions	Yield
In tetrahydrofuran at 120℃; under 5171.62 Torr; aza-Wittig reaction; solid phase reaction;	100%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 16308-07-9
4,5-dimethoxy-2-nitrobenzohydrazide

: C20H17ClN4O6

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 20℃;	100%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 2-chloro-7-methoxyquinoline-3-carboxaldoxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 0.333333h;	98%
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 0.166667h;	79%

: 372-19-0
meta-fluoroaniline

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 1122022-22-3
C17H12ClFN2O

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 0.416667h;	96.2%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 95-53-4
o-toluidine

: 1122022-29-0
C18H15ClN2O

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 0.333333h;	96.2%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 107-21-1
ethylene glycol

: 654634-98-7
2-chloro-3-[1,3]dioxolan-2-yl-7-methoxy-quinoline

Conditions

Conditions	Yield
With molecular sieve; toluene-4-sulfonic acid In toluene Heating;	96%
With montmorillonite K10 In toluene

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 536-74-3
phenylacetylene

: 7-methoxy-2-phenylethynyl-quinoline-3-carbaldehyde

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; Sonogashira reaction;	96%
With copper(l) iodide; bis(tri-phenylphosphine)palladium(II) dichloride; triethylamine In N,N-dimethyl-formamide at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;	91%
With triethylamine; triphenylphosphine; palladium dichloride In acetonitrile at 80℃; for 3h; Sonogashira coupling; Inert atmosphere;	88%

: 67-56-1
methanol

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 95395-23-6
2,7-dimethoxyquinoline-3-carboxaldehyde

Conditions

Conditions	Yield
With sodium hydroxide for 2h; Reflux;	95%
With potassium hydroxide In methanol Heating;	65%
With sodium at 40℃;

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 333408-48-3
3-(hydroxymethyl)-2-chloro-7-methoxyquinoline

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃;	95%
With methanol; sodium tetrahydroborate at 20℃; for 0.5h;	85%
With sodium tetrahydroborate In methanol at 20℃;
With sodium tetrahydroborate In methanol at 20℃;
With sodium tetrahydroborate In methanol at 20℃;

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 61-82-5
4H-1,2,4-triazol-3-amine

: 1256564-29-0
C13H9N5O

Conditions

Conditions	Yield
With silica gel; potassium carbonate for 0.283333h; Neat (no solvent); Microwave irradiation;	94%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 5805-39-0
2-(aminophenyl)benzimidazole

: C24H17ClN4O

Conditions

Conditions	Yield
In ethanol for 4h; Reflux;	93.5%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 2231-57-4
Thiocarbohydrazide

: 941592-71-8
2-hydrazino-9-methoxy[1,3,4]thiadiazepino[7,6-b]quinoline

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 0.0666667h; Microwave irradiation;	93%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 1-(2-chloro-7-methoxyquinolin-3-yl)-2,2,2-trifluoroethanol

Conditions

Conditions	Yield
With cesium fluoride In toluene at 0 - 20℃; for 15h;	93%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 558-13-4
carbon tetrabromide

: 2-chloro-3-(2,2-dibromovinyl)-7-methoxy-quinoline

Conditions

Conditions	Yield
With triphenylphosphine In dichloromethane at 0℃;	92%
With triphenylphosphine In dichloromethane at 0℃; for 1h;	92%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 98-80-6
phenylboronic acid

: 1254366-20-5
7-methoxy-2-phenylquinoline-3-carbaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate In water; benzene at 80℃; for 3h; Suzuki Coupling; Inert atmosphere;	92%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 106-95-6
allyl bromide

: 2-chloro-3-(1-hydroxybut-3-en-1-yl)-7-methoxyquinoline

Conditions

Conditions	Yield
With indium In water at 20℃;	91%
With indium In water; N,N-dimethyl-formamide at 20℃;

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: C21H21NPPol

: C20H19ClN2O

Conditions

Conditions	Yield
In tetrahydrofuran; acetonitrile at 120℃; under 5171.62 Torr; aza-Wittig reaction; solid phase reaction;	91%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 101382-55-2
7-methoxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehyde

Conditions

Conditions	Yield
With acetic acid for 10h; Heating;	90%
With acetic acid In water Heating;	87%
With hydrogenchloride for 1h; Heating;	86%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 134469-07-1
Benzimidazol-2-thiol

: 9-methoxy-13-hydroxy-13H-benzimidazo<2',1':2,3><1,3>thiazino<6,5-b>quinoline

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 15h;	90%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 533-58-4
2-Iodophenol

: 2-(2-iodophenoxy)-7-methoxyquinoline-3-carbaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	90%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 105-56-6
ethyl 2-cyanoacetate

: 1127335-63-0
C16H13ClN2O3

Conditions

Conditions	Yield
With cellulose sulfuric acid at 20℃; for 0.166667h; Knoevenagel condensation; Neat (no solvent); Grinding;	89%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 3-(3-formyl-7-methoxy-quinolin-2-yl)acrylic acid methyl ester

Conditions

Conditions	Yield
With sodium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium dichloride In N,N-dimethyl acetamide at 130℃; for 1.5h; Reagent/catalyst; Solvent; Temperature; Heck Reaction; Inert atmosphere;	89%

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 880105-67-9
7-methoxy-3-formyl-2-mercaptoquinoline

Conditions

Conditions	Yield
With hydrogenchloride; sodium sulfide In ethanol Heating;	88%
With sodium sulfide In ethanol

: 85-44-9
phthalic anhydride

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 126-81-8
dimedone

: C27H22ClN3O4

Conditions

Conditions	Yield
With Pr0.1CoFe1.9O4; hydrazine hydrate In ethanol for 1h; Reflux;	88%

...Expand

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 2-chloro-7-methoxyquinoline-3-carboxalehyde hydrazone

Conditions

Conditions	Yield
With sodium acetate; hydrazine hydrate In ethanol for 0.25h; Heating;	86%
With hydrazine hydrate

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 1663-39-4
tert-Butyl acrylate

: 3-(3-formyl-7-methoxy-quinolin-2-yl)acrylic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium dichloride In N,N-dimethyl acetamide at 130℃; Heck Reaction; Inert atmosphere;	86%

: 118-48-9
isatoic anhydride

: 68236-20-4
2-chloro-7-methoxyquinoline-3-carbaldehyde

: 2-(2-chloro-7-methoxyquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With titanium silicon oxide; ammonium acetate In water at 100℃; for 4h; Green chemistry;	86%

3-Quinolinecarboxaldehyde,2-chloro-7-methoxy- Specification

The 3-Quinolinecarboxaldehyde,2-chloro-7-methoxy-, with the CAS registry number 68236-20-4, is also known as 2-Chloro-3-formyl-7-methoxyquinoline. This chemical's molecular formula is C₁₁H₈ClNO₂ and formula weight is 221.64. What's more, its IUPAC name is 2-chloro-7-methoxyquinoline-3-carbaldehyde.

Physical properties of 3-Quinolinecarboxaldehyde,2-chloro-7-methoxy- are: (1)ACDLogP: 2.6; (2)#H bond donors: 0; (3)#H bond acceptors: 3; (4)#Freely Rotating Bonds: 2; (5)Polar Surface Area: 39.2 Å²; (6)Heavy Atom Count: 15; (7)Complexity: 237; (8)Covalently-Bonded Unit Count: 1; (9)Density: 1.348 g/cm³; (10)Flash Point: 179.9 °C; (11)Boiling Point: 379.9°C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: COC1=CC2=NC(=C(C=C2C=C1)C=O)Cl
(2)InChI: InChI=1S/C11H8ClNO2/c1-15-9-3-2-7-4-8(6-14)11(12)13-10(7)5-9/h2-6H,1H3
(3)InChIKey: WRXZCLBKDXISQA-UHFFFAOYSA-N

Product Name

2-CHLORO-7-METHOXY-QUINOLINE-3-CARBALDEHYDE

Synthetic route

3-Quinolinecarboxaldehyde,2-chloro-7-methoxy- Specification

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