Product Name

  • Name

    CIVENTICHEM CV-4057

  • EINECS 692-155-1
  • CAS No. 248281-84-7
  • Article Data19
  • CAS DataBase
  • Density 1.396 g/cm3
  • Solubility
  • 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
  • Appearance
  • 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-;
  • PSA 87.42000
  • LogP 3.09358

Synthetic route

1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
637027-41-9

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

N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

laquinimod
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%
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
637027-41-9

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

N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

A

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

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

B

laquinimod
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%
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
637027-41-9

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

N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

A

methanol
67-56-1

methanol

B

laquinimod
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

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

laquinimod
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%
N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
335640-50-1

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

laquinimod
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;
methyl 2-chloro-6-[[3-(ethyl(phenyl)amino)-3-oxopropanoyl]methylamino]benzoate
1379595-99-9

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

laquinimod
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%
5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester
248282-10-2

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

laquinimod
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
5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione
20829-96-3

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

laquinimod
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
2-chloro-6-aminobenzoic acid
2148-56-3

2-chloro-6-aminobenzoic acid

laquinimod
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
5-chloro-N-methylisatoic anhydride
40707-01-5

5-chloro-N-methylisatoic anhydride

laquinimod
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
N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester
248282-10-2

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

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
In n-heptane
1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
637027-41-9

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

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
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
103-69-5

N-ethyl-N-phenylamine

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
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
118081-77-9

3-(Ethyl(phenyl)amino)-3-oxopropanoic acid

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
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
142613-14-7

methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
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
C10H10ClNO4

C10H10ClNO4

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
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
40707-01-5

5-chloro-N-methylisatoic anhydride

methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate
142613-14-7

methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate

laquinimod
248281-84-7

laquinimod

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl acetamide; mineral oil at 85℃; for 7h; Inert atmosphere;110 g
laquinimod
248281-84-7

laquinimod

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

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

Conditions
ConditionsYield
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
248281-84-7

laquinimod

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

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

Conditions
ConditionsYield
With calcium acetate In ethanol; water at 70℃; for 0.5h;98%
laquinimod
248281-84-7

laquinimod

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

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

Conditions
ConditionsYield
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
248281-84-7

laquinimod

1H,3H-spiro[5-chloro-1-methylquinoline-2,4-dione-3,3'-[1]ethylindolin-[2]-one]

1H,3H-spiro[5-chloro-1-methylquinoline-2,4-dione-3,3'-[1]ethylindolin-[2]-one]

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; acetic acid In ethanol at 20℃; for 1h;95%
L-lysine
56-87-1

L-lysine

laquinimod
248281-84-7

laquinimod

laquinimod L-lysine salt

laquinimod L-lysine salt

Conditions
ConditionsYield
In methanol Solvent;92.7%
aniline
62-53-3

aniline

laquinimod
248281-84-7

laquinimod

ABR-215174

ABR-215174

Conditions
ConditionsYield
In toluene at 100℃; for 1h;92%
laquinimod
248281-84-7

laquinimod

N-ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide iron (III) salt

N-ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide iron (III) salt

Conditions
ConditionsYield
With iron(III) sulfate In chloroform; water at 40℃;85%
cholin hydroxide
123-41-1

cholin hydroxide

laquinimod
248281-84-7

laquinimod

laquinimod choline hydroxide salt
1609005-03-9

laquinimod choline hydroxide salt

Conditions
ConditionsYield
In methanol for 0.166667h; Solvent;76.3%
methanol
67-56-1

methanol

laquinimod
248281-84-7

laquinimod

1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
637027-41-9

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

Conditions
ConditionsYield
at 100℃; for 0.1h; microwave irradiation;
methanol
67-56-1

methanol

laquinimod
248281-84-7

laquinimod

A

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

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

B

1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
637027-41-9

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
335640-50-1

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

Conditions
ConditionsYield
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics;
propan-1-ol
71-23-8

propan-1-ol

laquinimod
248281-84-7

laquinimod

A

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

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

B

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

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

C

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
335640-50-1

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

Conditions
ConditionsYield
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics; Further Variations:; reaction partner content;
ethanol
64-17-5

ethanol

laquinimod
248281-84-7

laquinimod

A

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

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

B

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
335640-50-1

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
248282-10-2

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

Conditions
ConditionsYield
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics; Further Variations:; Reagents;
isopropyl alcohol
67-63-0

isopropyl alcohol

laquinimod
248281-84-7

laquinimod

A

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

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

B

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

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

C

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
335640-50-1

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

Conditions
ConditionsYield
With water; trifluoroacetic acid In dimethyl sulfoxide; acetonitrile at 50℃; for 2h; Kinetics;
laquinimod
248281-84-7

laquinimod

A

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

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

B

5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid
335640-50-1

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

Conditions
ConditionsYield
In water; toluene at 100℃; for 1h;
laquinimod
248281-84-7

laquinimod

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

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

Conditions
ConditionsYield
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
248281-84-7

laquinimod

5-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid methyl ester

5-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid methyl ester

Conditions
ConditionsYield
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
71-23-8

propan-1-ol

laquinimod
248281-84-7

laquinimod

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

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

Conditions
ConditionsYield
With hydrogenchloride In water at 45 - 60℃; for 4h; Reactivity;
Reflux;
With hydrogenchloride at 45 - 60℃; for 4h; Reactivity;

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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