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CAS No.: | 248282-01-1 |
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Name: | Paquinimod |
Article Data: | 4 |
Molecular Structure: | |
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 |
1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester
N-ethyl-N-phenylamine
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
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In n-heptane for 2h; Product distribution / selectivity; Reflux; Molecular sieve; | 93% |
N-ethyl-N-phenylamine
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
---|---|
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 4.5h; |
5-ethyl-1H-benzo[d][1,3]oxazine-2,4-dione
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
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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 |
6-ethyl-anthranilic acid
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
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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 |
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
---|---|
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 |
ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
---|---|
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 |
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
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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% |
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 lithium salt
Conditions | Yield |
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With lithium hydroxide In ethanol; water for 4h; | 84% |
With lithium hydroxide In ethanol; water for 4h; | 84% |
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
---|---|
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% |
propan-1-ol
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Conditions | Yield |
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With hydrogenchloride In water at 45 - 60℃; for 4h; Reactivity; | |
With hydrogenchloride at 45 - 60℃; for 4h; Reactivity; |