4-Hydroxy-4-methyl-2-pentanone
2-amino-4-chlorobenzaldehyde
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate In toluene at 70℃; Inert atmosphere; Schlenk technique; chemoselective reaction; | 90% |
Conditions | Yield |
---|---|
With phospho-tungstic acid; phosphotungstic acid; silica gel for 0.2h; Doebner-Miller reaction; microwave irradiation; | 86% |
With hydrogenchloride; chloranil In tetrahydrofuran; methanol; iso-butanol |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With tetrasodium cobalt(II) 4,4',4'',4'''-tetrasulphophthalocyanine In water; ethyl acetate at 20℃; for 18h; Irradiation; Green chemistry; | 85% |
With rose bengal; oxygen In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation; | 73% |
With rose bengal In N,N-dimethyl acetamide at 20℃; for 28h; Irradiation; | 73% |
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; Co(dmgH)2(4-MeCO2Py)Cl In water at 28℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; | 73% |
With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide In tert-Amyl alcohol at 95℃; for 48h; | 42% |
Conditions | Yield |
---|---|
With magnetite-palladium-graphene nanocomposite In acetonitrile at 80℃; for 12h; | 72% |
ethanol
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate In tetrachloromethane at 140℃; for 4h; Autoclave; Inert atmosphere; Sealed tube; | A 11% B 67% |
Conditions | Yield |
---|---|
Stage #1: 3-chloro-aniline; crotonaldehyde With hydrogenchloride In water; toluene at 110℃; for 1.5h; Stage #2: With zinc(II) chloride In tetrahydrofuran; water; acetone; toluene at 60℃; for 1h; Cooling with ice; | 30% |
With hydrogenchloride In water; toluene for 2h; Doebner-Miller Quinoline Synthesis; Reflux; | |
With hydrogenchloride; 1-methyl-2-nitrobenzene In water at 100℃; for 9h; Reagent/catalyst; Skraup Quinoline Synthesis; Reflux; |
1,1,3-trimethoxybutane
3-chloroaniline hydrochloride
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With ethanol; iron(III) chloride; zinc(II) chloride |
Conditions | Yield |
---|---|
With hydrogenchloride |
acetaldehyde
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With di-μ-chlorobis(norbornadiene)dirhodium(I); 3-Nitrochlorobenzene In ethanol at 180℃; for 4h; Yield given. Yields of byproduct given; |
β-(m-chloroanilino)crotonaldehyde
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; Rate constant; |
formaldehyd
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With sulfuric acid; sodium 3-nitrobenzenesulfonate at 120 - 130℃; for 1.83333h; | A 8.64 g B 0.28 g |
With sulfuric acid; sodium 3-nitrobenzenesulfonate at 120 - 130℃; for 1.83333h; | A 8.64 g B 0.79 g |
trans-Crotonaldehyde
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With hydrogenchloride; chloranil In various solvent(s) for 0.333333h; Heating; |
Conditions | Yield |
---|---|
at 120 - 130℃; Behandeln mit Paraldehyd; Trennung der Isomeren ueber die Pikrate; |
trans-Crotonaldehyde
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
C
N-ethyl-3-chloroaniline
D
Butyl-(3-chloro-phenyl)-amine
Conditions | Yield |
---|---|
With hydrogenchloride; chloranil In ethanol; water Product distribution; Heating; other substituted anilines; var. solvents, var. oxidants and acids, var. temperatures; |
1-(m-chlorophenylamino)-3-(m-chlorophenylimino)-1-butene hydrochloride
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.29 g / NaOH / H2O; ethanol / 2 h / 80 °C 2: 8.64 g / sodium m-nitrobenzenesulfonate, 72.2 percent H2SO4 / 1.83 h / 120 - 130 °C View Scheme |
Conditions | Yield |
---|---|
zinc(II) chloride In hydrogenchloride; water |
ethyl vinyl ether
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
N-ethyl-3-chloroaniline
Conditions | Yield |
---|---|
With palladium on activated charcoal; palladium dichloride In acetonitrile at 80℃; for 24h; | A 68 %Chromat. B 23 %Chromat. |
(E)-1-Bromo-2-butene
3,3'-dichloroazobenzene
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With copper(l) iodide In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Sealed tube; Overall yield = 44 %; Overall yield = 15.6 mg; |
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper(I) bromide; pyridine / toluene / 20 h / 60 °C 2: copper(l) iodide / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube View Scheme |
ethylene glycol
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
Conditions | Yield |
---|---|
With tetrachloromethane; iron(III) chloride hexahydrate at 150℃; for 8h; Inert atmosphere; Sealed tube; Autoclave; Overall yield = 56 %; |
1.3-butanediol
3-chloro-aniline
A
2-methyl-7-chloroquinoline
B
2-methyl-5-chloroquinoline
C
7-chloro-4-methyl-quinoline
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate In tetrachloromethane at 150℃; for 8h; Inert atmosphere; Overall yield = 79 %; |
(2-amino-4-chlorophenyl)methanol
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: manganese(IV) oxide / dichloromethane / Inert atmosphere 2: chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate / toluene / 70 °C / Inert atmosphere; Schlenk technique View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / Inert atmosphere 3: chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate / toluene / 70 °C / Inert atmosphere; Schlenk technique View Scheme |
A
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With monoamine oxidase from Pseudomonas monteilii ZMU-T01 In aq. buffer at 37℃; pH=7.5; Resolution of racemate; enantioselective reaction; | A n/a B n/a |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dichloromethane / 5 h / 40 °C / Acidic conditions 2: sulfuric acid / toluene; water / 100 °C 3: water / 70 °C View Scheme |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
In water at 70℃; Temperature; Reagent/catalyst; |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at -10℃; Green chemistry; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With {Au(dppm)}2Cl2; trifluoroacetic acid In methanol Inert atmosphere; UV-irradiation; | 99% |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With hydrogen In toluene at 100℃; under 37503.8 Torr; for 24h; chemoselective reaction; | 99% |
With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In toluene; acetonitrile at 100℃; under 22801.5 Torr; for 48h; Autoclave; Glovebox; chemoselective reaction; | 87% |
With sodium tetrahydroborate; hydrogen; cobalt(II) chloride In water at 150℃; under 30003 Torr; for 17h; Green chemistry; chemoselective reaction; | 67% |
With sodium cyanoborohydride; acetic acid at 20℃; Sealed tube; |
2-methyl-7-chloroquinoline
(-)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline
Conditions | Yield |
---|---|
With bromopentacarbonylmanganese(I); potassium tert-butylate; hydrogen; E-1-(1H-benzo[d]imidazol-2-yl)-N-((SC,RFC)-1-(2-diphenylphosphino)ferrocenyl)methanimine In 1,4-dioxane at 80℃; under 45004.5 Torr; for 16h; Autoclave; enantioselective reaction; | 98% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C73H100O2P2; hydrogen; iodine In toluene at 20℃; under 15201 Torr; for 24h; optical yield given as %ee; enantioselective reaction; |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; N1-benzyl-N2-(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With C51H57ClNiO2P2; sodium t-butanolate at 25℃; | 98% |
2-methyl-7-chloroquinoline
Isophthalaldehyde
(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde
Conditions | Yield |
---|---|
With lanthanum pentafluorobenzoate In toluene at 120℃; for 24h; | 97% |
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry; | 93% |
With acetic anhydride In toluene at 100 - 105℃; for 12 - 15h; | 75.15% |
2-methyl-7-chloroquinoline
N-Benzylaniline
(E)-7-chloro-2-styrylquinoline
Conditions | Yield |
---|---|
Stage #1: N-Benzylaniline With 2,3-dicyano-5,6-dichloro-p-benzoquinone In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-methyl-7-chloroquinoline In N,N-dimethyl-formamide at 70℃; for 24h; Inert atmosphere; diastereoselective reaction; | 97% |
Conditions | Yield |
---|---|
With lanthanum pentafluorobenzoate In toluene at 120℃; for 24h; | 97% |
With tert.-butylhydroperoxide; N-Bromosuccinimide In water; acetonitrile at 100℃; for 48h; Schlenk technique; Darkness; Green chemistry; | 95% |
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 80℃; under 760.051 Torr; for 24h; | 86% |
With tert.-butylhydroperoxide; water; sodium chloride at 100℃; | 75% |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With water-d2; benzoic acid at 80℃; for 4h; | 97% |
With water-d2; benzoic acid at 90℃; for 8h; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
With (PhPAd-DalPhos)NiCl(o-tol); sodium t-butanolate In toluene at 25℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With 2-Picolinic acid; ferrous(II) sulfate heptahydrate; sodium bromate In water; dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation; | 97% |
Conditions | Yield |
---|---|
With (4,4′-di-tert-butyl-2,2′-dipyridyl)Ni(o-tolyl)(Br); 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 80℃; for 12h; Inert atmosphere; Sealed tube; UV-irradiation; | 97% |
Conditions | Yield |
---|---|
With C33H43ClNiO6P2; sodium t-butanolate In toluene at 25℃; for 18h; Inert atmosphere; Sealed tube; | 97% |
2-methyl-7-chloroquinoline
benzaldehyde
(E)-7-chloro-2-styrylquinoline
Conditions | Yield |
---|---|
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry; | 96% |
With cobalt(II) chloride In water at 120℃; for 24h; | 93% |
With 1,3-dimethylbarbituric acid; acetic acid In 1,4-dioxane; water at 60℃; for 24h; | 93% |
2-methyl-7-chloroquinoline
2-methylquinolin-7-amine
Conditions | Yield |
---|---|
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; | 96% |
With bis(1,5-cyclooctadiene)nickel (0); (R)-1-[(Sp)-2-(dicyclohexylphosphanyl)ferrocenyl]ethyldicyclohexylphosphane; ammonia; sodium t-butanolate In 1,4-dioxane; toluene at 105℃; under 5895.64 - 7757.43 Torr; for 18h; Sealed tube; | 92% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); N,N,N,N,-tetramethylethylenediamine; C38H62P2 In tetrahydrofuran at 20℃; for 16h; Negishi Coupling; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tetrahydrofuran at 20℃; for 0.5h; Suzuki-Miyaura Coupling; | 95% |
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With diethyl amine hydrochloride; triethylamine In 1,4-dioxane at 100℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; | 95% |
Conditions | Yield |
---|---|
With iodine; oxygen In dimethyl sulfoxide at 110℃; | 95% |
2-methyl-7-chloroquinoline
tetramethylammonium trifluoromethylselenate(0)
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In toluene at 50℃; for 12h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With η3-1-tert-butylindenyl palladium chloride dimer In toluene at 70℃; for 4h; Hiyama Coupling; Inert atmosphere; Glovebox; Sealed tube; | 94% |
methanol
2-methyl-7-chloroquinoline
7-chloro-4-(hydroxymethyl)-2-methylquinoline
Conditions | Yield |
---|---|
With silver nitrate; Selectfluor In water at 80℃; for 4h; Sealed tube; | 94% |
With sodium persulfate In water at 80℃; for 4h; Reagent/catalyst; Inert atmosphere; | 85% |
With ferrous(II) sulfate heptahydrate; sulfuric acid; hydroxylamine-O-sulfonic acid In water for 3h; | 78% |
2-methyl-7-chloroquinoline
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine; (((1R,3S,3'S)-3,3'-diethyl-3H,3'H-1,1'-spirobi[isobenzofuran]-7,7'-diyl)bis(oxy))bis(diphenylphosphane) In tetrahydrofuran at 20℃; under 18100.7 Torr; for 10h; Inert atmosphere; enantioselective reaction; | 94% |
2-methyl-7-chloroquinoline
methyl 2-(3-(3-formylphenyl)-3-oxopropyl)benzoate
methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate
Conditions | Yield |
---|---|
With acetic anhydride at 140℃; for 8h; | 93% |
Conditions | Yield |
---|---|
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry; | 93% |
Conditions | Yield |
---|---|
With benzophenone In acetone at 20℃; for 4h; Microwave irradiation; | 93% |
2-methyl-7-chloroquinoline
7-chloro-quinoline-2-carbaldehyde
Conditions | Yield |
---|---|
With selenium(IV) oxide In 1,4-dioxane at 60℃; Inert atmosphere; | 92% |
With selenium(IV) oxide In 1,4-dioxane for 2.5h; Oxidation; Heating; | 84% |
With selenium(IV) oxide; water In tetrahydrofuran at 25℃; for 6h; | 78% |
Molecular Structure:
Molecular Formula: C10H8ClN
Molecular Weight: 177.6302
IUPAC Name: 7-Chloro-2-methylquinoline
Synonyms of 7-Chloroquinaldine (CAS NO.4965-33-7): Quinoline, 7-chloro-2-methyl-
CAS NO: 4965-33-7
Product Categories: Quinolines, Quinazolines and derivatives ; Halides ; Quinolines, Isoquinolines & Quinoxalines ; Quinoline&Isoquinoline ; API ; Alkylquinolines ; Haloquinolines ; Quinolines ; Quinolines, Isoquinolines & Quinoxalines
Melting point: 74-78 °C
Polar Surface Area: 12.89 Å2
Index of Refraction: 1.634
Molar Refractivity: 51.9 cm3
Molar Volume: 144.9 cm3
Surface Tension: 46.5 dyne/cm
Density: 1.225 g/cm3
Flash Point: 148.7 °C
Enthalpy of Vaporization: 49.6 kJ/mol
Boiling Point: 278.2 °C at 760 mmHg
Vapour Pressure: 0.00732 mmHg at 25°C
7-Chloroquinaldine (CAS NO.4965-33-7) is used as a Pharmaceutical intermediates.
Safety Information of 7-Chloroquinaldine (CAS NO.4965-33-7):
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3
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