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Laquinimod
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Name

Laquinimod

 EINECS 692-155-1
CAS No. 248281-84-7 Density 1.396 g/cm3
PSA 87.42000 LogP 3.09358
Solubility N/A Melting Point 201 °C (decomp)
Formula C19H17ClN2O3 Boiling Point 484.799 °C at 760 mmHg
Molecular Weight 356.809 Flash Point 246.998 °C
Transport Information N/A Appearance N/A
Safety 45 Risk Codes 25
Molecular Structure Molecular Structure of 248281-84-7 (CIVENTICHEM CV-4057) Hazard Symbols T
Synonyms

ABR 215062;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-;

Article Data 19

Laquinimod Synthetic route

637027-41-9

1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester

103-69-5

N-ethyl-N-phenylamine

248281-84-7

laquinimod

Conditions
ConditionsYield
In n-heptane for 6.58333h; Heating;98%
In n-heptane98%
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%
637027-41-9

1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester

103-69-5

N-ethyl-N-phenylamine

A

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline

B

248281-84-7

laquinimod

Conditions
ConditionsYield
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%
637027-41-9

1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester

103-69-5

N-ethyl-N-phenylamine

A

67-56-1

methanol

B

248281-84-7

laquinimod

Conditions
ConditionsYield
In n-heptane for 6.58333h; Product distribution / selectivity; Heating / reflux;A n/a
B 98%

5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide sodium salt

248281-84-7

laquinimod

Conditions
ConditionsYield
With hydrogenchloride In water96%
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%
103-69-5

N-ethyl-N-phenylamine

335640-50-1

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid

248281-84-7

laquinimod

Conditions
ConditionsYield
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;
1379595-99-9

methyl 2-chloro-6-[[3-(ethyl(phenyl)amino)-3-oxopropanoyl]methylamino]benzoate

248281-84-7

laquinimod

Conditions
ConditionsYield
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%
248282-10-2

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester

248281-84-7

laquinimod

Conditions
ConditionsYield
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
20829-96-3

5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione

248281-84-7

laquinimod

Conditions
ConditionsYield
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
2148-56-3

2-chloro-6-aminobenzoic acid

248281-84-7

laquinimod

Conditions
ConditionsYield
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
40707-01-5

5-chloro-N-methylisatoic anhydride

248281-84-7

laquinimod

Conditions
ConditionsYield
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

Laquinimod Chemical Properties


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 Specification

 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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