1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
N-ethyl-N-phenylamine
laquinimod
Conditions | Yield |
---|---|
In n-heptane for 6.58333h; Heating; | 98% |
In n-heptane | 98% |
In n-heptane for 4h; Product distribution / selectivity; Reflux; Molecular sieve; | 98% |
In n-heptane for 6h; Reflux; | 97% |
In octane; n-heptane at 112℃; for 5h; Inert atmosphere; Large scale; | 96% |
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
N-ethyl-N-phenylamine
B
laquinimod
Conditions | Yield |
---|---|
In n-heptane Heating / reflux; | A n/a B 98% |
In toluene Heating / reflux; | A n/a B 98% |
In n-heptane for 6.58333h; Heating / reflux; | A 0.03% B 98% |
In toluene for 3.25h; Heating / reflux; | A 0.54% B 90% |
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
N-ethyl-N-phenylamine
A
methanol
B
laquinimod
Conditions | Yield |
---|---|
In n-heptane for 6.58333h; Product distribution / selectivity; Heating / reflux; | A n/a B 98% |
laquinimod
Conditions | Yield |
---|---|
With hydrogenchloride In water | 96% |
Stage #1: 5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide sodium salt With sodium hydroxide In water at 50℃; pH=12.5; Stage #2: With hydrogenchloride In ethanol; water at 4℃; pH=5; Product distribution / selectivity; | 56.2% |
N-ethyl-N-phenylamine
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
laquinimod
Conditions | Yield |
---|---|
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 4.5h; | 87% |
With dicyclohexyl-carbodiimide In toluene at 80℃; for 4h; Reagent/catalyst; Inert atmosphere; Large scale; | 62% |
Stage #1: N-ethyl-N-phenylamine With dichlorotriphenylphosphorane In chloroform at 25 - 30℃; for 0.25h; Inert atmosphere; Stage #2: 5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid In chloroform at 25 - 45℃; Product distribution / selectivity; |
methyl 2-chloro-6-[[3-(ethyl(phenyl)amino)-3-oxopropanoyl]methylamino]benzoate
laquinimod
Conditions | Yield |
---|---|
Stage #1: methyl 2-chloro-6-[[3-(ethyl(phenyl)amino)-3-oxopropanoyl]methylamino]benzoate With sodium methylate In tetrahydrofuran; methanol for 2h; Inert atmosphere; Reflux; Stage #2: With water; sodium hydroxide In methanol at 5℃; for 0.5h; Stage #3: With hydrogenchloride In methanol; water Product distribution / selectivity; | 87% |
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.1 h / 100 °C / microwave irradiation 2: 98 percent / heptane / 6.58 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 91 percent / HCl / acetic acid / 6 h / 60 °C 2: 87 percent / SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C View Scheme |
5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: NaH / dimethylformamide / 5 h / 20 °C 2: NaH / dimethylformamide / 5 h / 85 °C 3: 91 percent / HCl / acetic acid / 6 h / 60 °C 4: 87 percent / SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium carbonate / N,N-dimethyl-formamide / 1.25 h / 0 - 30 °C / Inert atmosphere 2.1: sodium methylate / N,N-dimethyl-formamide / 1.5 h / 25 - 85 °C / Inert atmosphere 2.2: 1.17 h / 80 - 85 °C 2.3: 2 h / 25 - 30 °C / pH 1 3.1: hydrogenchloride; acetic acid / 80 - 85 °C 4.1: dichlorotriphenylphosphorane / dichloromethane / 0.25 h / 25 - 30 °C / Inert atmosphere 4.2: 3 h / 25 - 45 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 45 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 7 h / 85 °C / Inert atmosphere View Scheme |
2-chloro-6-aminobenzoic acid
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: dioxane / 1 h / 20 °C 2: NaH / dimethylformamide / 5 h / 20 °C 3: NaH / dimethylformamide / 5 h / 85 °C 4: 91 percent / HCl / acetic acid / 6 h / 60 °C 5: 87 percent / SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 1,4-dioxane / 12 - 20 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 45 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 7 h / 85 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 1,4-dioxane / 12 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 72 h / 20 °C / Inert atmosphere; Large scale 3: sodium hydride / mineral oil; N,N-dimethyl acetamide / 7 h / 85 °C / Inert atmosphere View Scheme |
5-chloro-N-methylisatoic anhydride
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaH / dimethylformamide / 5 h / 85 °C 2: 91 percent / HCl / acetic acid / 6 h / 60 °C 3: 87 percent / SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium methylate / N,N-dimethyl-formamide / 1.5 h / 25 - 85 °C / Inert atmosphere 1.2: 1.17 h / 80 - 85 °C 1.3: 2 h / 25 - 30 °C / pH 1 2.1: hydrogenchloride; acetic acid / 80 - 85 °C 3.1: dichlorotriphenylphosphorane / dichloromethane / 0.25 h / 25 - 30 °C / Inert atmosphere 3.2: 3 h / 25 - 45 °C View Scheme | |
Multi-step reaction with 2 steps 1: mineral oil; N,N-dimethyl acetamide / 5 h / 85 °C / Inert atmosphere 2: n-heptane; octane / 5 h / 112 °C / Inert atmosphere; Large scale View Scheme | |
Multi-step reaction with 3 steps 1: mineral oil; N,N-dimethyl acetamide / 5 h / 85 °C / Inert atmosphere 2: hydrogenchloride; acetic acid; water / acetic anhydride / 2 h / 20 - 85 °C / Inert atmosphere; Large scale 3: dicyclohexyl-carbodiimide / toluene / 4 h / 80 °C / Inert atmosphere; Large scale View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 1.2: 5 h / 80 °C 2.1: n-heptane / 6 h / Reflux View Scheme |
N-ethyl-N-phenylamine
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester
laquinimod
Conditions | Yield |
---|---|
In n-heptane |
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; acetic acid / 80 - 85 °C 2.1: dichlorotriphenylphosphorane / dichloromethane / 0.25 h / 25 - 30 °C / Inert atmosphere 2.2: 3 h / 25 - 45 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride; acetic acid; water / acetic anhydride / 2 h / 20 - 85 °C / Inert atmosphere; Large scale 2: dicyclohexyl-carbodiimide / toluene / 4 h / 80 °C / Inert atmosphere; Large scale View Scheme |
N-ethyl-N-phenylamine
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: dichloromethane / 14 h / 20 °C / Inert atmosphere 2.1: water; lithium hydroxide / tetrahydrofuran / 1.5 h / 20 °C 2.2: 0 - 5 °C / pH 2 - 3 3.1: pyridine / dichloromethane / 0.5 h / 20 - 25 °C / Inert atmosphere 3.2: 1 h / 0 - 5 °C 3.3: 0 - 20 °C 4.1: sodium methylate / tetrahydrofuran; methanol / 2 h / Inert atmosphere; Reflux 4.2: 0.5 h / 5 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / acetone / 2 h / 2 - 20 °C / Inert atmosphere 2: sodium hydride / mineral oil; N,N-dimethyl acetamide / 7 h / 85 °C / Inert atmosphere View Scheme |
3-(Ethyl(phenyl)amino)-3-oxopropanoic acid
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane / 0.5 h / 20 - 25 °C / Inert atmosphere 1.2: 1 h / 0 - 5 °C 1.3: 0 - 20 °C 2.1: sodium methylate / tetrahydrofuran; methanol / 2 h / Inert atmosphere; Reflux 2.2: 0.5 h / 5 °C View Scheme |
methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: water; lithium hydroxide / tetrahydrofuran / 1.5 h / 20 °C 1.2: 0 - 5 °C / pH 2 - 3 2.1: pyridine / dichloromethane / 0.5 h / 20 - 25 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C 2.3: 0 - 20 °C 3.1: sodium methylate / tetrahydrofuran; methanol / 2 h / Inert atmosphere; Reflux 3.2: 0.5 h / 5 °C View Scheme |
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1,4-dioxane / 10 h / 45 °C / Inert atmosphere; Large scale 2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 45 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 7 h / 85 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: acetyl chloride / 1,4-dioxane / 10 h / 45 °C / Inert atmosphere; Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 72 h / 20 °C / Inert atmosphere; Large scale 3: sodium hydride / mineral oil; N,N-dimethyl acetamide / 7 h / 85 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1,4-dioxane / 10 h / 45 °C / Inert atmosphere; Large scale 2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 45 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: mineral oil; N,N-dimethyl acetamide / 5 h / 85 °C / Inert atmosphere 4.1: n-heptane; octane / 5 h / 112 °C / Inert atmosphere; Large scale View Scheme |
5-chloro-N-methylisatoic anhydride
methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate
laquinimod
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl acetamide; mineral oil at 85℃; for 7h; Inert atmosphere; | 110 g |
laquinimod
Conditions | Yield |
---|---|
In water; toluene at 140℃; for 4h; | 100% |
Multi-step reaction with 2 steps 1: toluene; H2O / 1 h / 100 °C 2: 98 percent / dimethylsulfoxide / 1.5 h / 70 °C View Scheme |
laquinimod
Conditions | Yield |
---|---|
With calcium acetate In ethanol; water at 70℃; for 0.5h; | 98% |
laquinimod
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 1.75h; Inert atmosphere; Large scale; | 95% |
With sodium methylate In methanol at 20 - 30℃; | 94% |
With sodium hydroxide In ethanol; water at 20℃; for 6.58333h; pH=8 - 12; | 90% |
laquinimod
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; acetic acid In ethanol at 20℃; for 1h; | 95% |
Conditions | Yield |
---|---|
In methanol Solvent; | 92.7% |
Conditions | Yield |
---|---|
In toluene at 100℃; for 1h; | 92% |
laquinimod
Conditions | Yield |
---|---|
With iron(III) sulfate In chloroform; water at 40℃; | 85% |
Conditions | Yield |
---|---|
In methanol for 0.166667h; Solvent; | 76.3% |
methanol
laquinimod
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
Conditions | Yield |
---|---|
at 100℃; for 0.1h; microwave irradiation; |
methanol
laquinimod
B
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
C
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics; |
propan-1-ol
laquinimod
C
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics; Further Variations:; reaction partner content; |
ethanol
laquinimod
B
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
C
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics; Further Variations:; Reagents; |
isopropyl alcohol
laquinimod
C
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics; |
laquinimod
B
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
In water; toluene at 100℃; for 1h; |
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.1 h / 100 °C / microwave irradiation 2: 37 percent / DBU / N,N-dimethyl-acetamide / 20 h / 20 °C View Scheme |
laquinimod
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.1 h / 100 °C / microwave irradiation 2: 39 percent / DBU / N,N-dimethyl-acetamide / 20 h / 20 °C View Scheme |
propan-1-ol
laquinimod
Conditions | Yield |
---|---|
With hydrogenchloride In water at 45 - 60℃; for 4h; Reactivity; | |
Reflux; | |
With hydrogenchloride at 45 - 60℃; for 4h; Reactivity; |
IUPAC Name: 5-Chloro-N-ethyl-2-hydroxy-1-methyl-4-oxo-N-phenylquinoline-3-carboxamide
Canonical SMILES: CCN(C1=CC=CC=C1)C(=O)C2=C(N(C3=C(C2=O)C(=CC=C3)Cl)C)O
InChI: InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,24H,3H2,1-2H3
InChIKey: PVTNCGYZIYKPJX-UHFFFAOYSA-N
Molecular Weight: 356.80288 [g/mol]
Molecular Formula: C19H17ClN2O3
XLogP3-AA: 4.3
H-Bond Donor: 1
H-Bond Acceptor: 4
Index of Refraction: 1.674
Molar Refractivity: 96.003 cm3
Molar Volume: 255.663 cm3
Surface Tension: 64.288 dyne/cm
Density: 1.396 g/cm3
Flash Point: 246.998 °C
Enthalpy of Vaporization: 79.015 kJ/mol
Boiling Point: 484.799 °C at 760 mmHg
Vapour Pressure of Laquinimod (CAS NO.248281-84-7): 0 mmHg at 25 °C
Laquinimod (CAS NO.248281-84-7), its Synonyms are 5-Chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide ; N-Ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide ; N-Ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide ; 3-Quinolinecarboxamide, 5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl- .
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