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248282-01-1

Basic Information
CAS No.: 248282-01-1
Name: Paquinimod
Article Data: 4
Molecular Structure:
Molecular Structure of 248282-01-1 (Paquinimod)
Formula: C21H22N2O3
Molecular Weight: 350.417
Synonyms: N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide;N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide;Paquinimod [INN];UNII-HB76GLG27V;Paquinimod;N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide;N-ethyl-N-phenyl-1,2-dihydro-5-ethyl-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide;
Density: 1.267g/cm3
Boiling Point: 487.259oC at 760 mmHg
Flash Point: 248.486oC
PSA: 62.54000
LogP: 3.47320
Synthetic route
1354639-60-3

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

103-69-5

N-ethyl-N-phenylamine

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

Conditions
ConditionsYield
In n-heptane for 2h; Product distribution / selectivity; Reflux; Molecular sieve;93%
103-69-5

N-ethyl-N-phenylamine

5-ethyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

Conditions
ConditionsYield
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 4.5h;
34934-06-0

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

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaH / dimethylformamide / 5 h / 20 °C
2: NaH / dimethylformamide / 5 h / 85 °C
3: HCl / acetic acid / 6 h / 60 °C
4: SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide
2: sodium methylate / N,N-dimethyl-formamide
3: n-heptane / 2 h / Reflux; Molecular sieve
View Scheme
66232-56-2

6-ethyl-anthranilic acid

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

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: HCl / acetic acid / 6 h / 60 °C
5: SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: chloroformic acid ethyl ester / 1,4-dioxane
2: potassium carbonate / N,N-dimethyl-formamide
3: sodium methylate / N,N-dimethyl-formamide
4: n-heptane / 2 h / Reflux; Molecular sieve
View Scheme

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

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaH / dimethylformamide / 5 h / 85 °C
2: HCl / acetic acid / 6 h / 60 °C
3: SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C
View Scheme
675574-87-5

ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / acetic acid / 6 h / 60 °C
2: SOCl2; Et3N / CH2Cl2 / 4.5 h / 0 - 20 °C
View Scheme
248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

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

Conditions
ConditionsYield
With sodium hydroxide; calcium acetate In ethanol; water at 20 - 70℃; for 1.08333h; pH=7.5;98%
Stage #1: N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide With sodium hydroxide In ethanol; water pH=7.5;
Stage #2: With calcium acetate In ethanol; water
98%
248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

862462-44-0

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

Conditions
ConditionsYield
With lithium hydroxide In ethanol; water for 4h;84%
With lithium hydroxide In ethanol; water for 4h;84%
248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

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

Conditions
ConditionsYield
With sodium hydroxide; zinc diacetate In ethanol; chloroform; water for 0.166667h;76%
Stage #1: N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide With sodium hydroxide In ethanol; water
Stage #2: With zinc diacetate In ethanol; chloroform; water for 0.166667h;
76%
71-23-8

propan-1-ol

248282-01-1

N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide

C16H19NO4

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