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Name: Nimodipine Synonyms: 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester CAS:66085-59-4 MF: C21H26N2O7 Appearance: white powder Storage:Store in cool and dry place, away from s
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inquiryisopropyl 3-aminocrotonate
(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate
nimodipin
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 81% |
2-methoxyethyl-3-oxobutanoate
3-nitro-benzaldehyde
isopropyl β-aminocrotonate
A
nimodipin
B
3,5-diisopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
Conditions | Yield |
---|---|
In ethanol for 16h; Heating; | A 69% B n/a |
isopropyl acetoacetate
2-methoxyethyl-3-oxobutanoate
3-nitro-benzaldehyde
nimodipin
Conditions | Yield |
---|---|
With pyridine; 4 A molecular sieve; polysterene-based acid-cleavable Rink amine resin; trifluoroacetic acid 1) CH2Cl2, rt, 3 d; 2) 45 deg C, 24 h; 3) CH2Cl2, 45 min;; Yield given. Multistep reaction; | |
With ammonium acetate In ethanol at 80℃; for 2h; Hantzsch Pyridine Synthesis; |
isopropyl acetoacetate
nimodipin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / NH3 (gas.) / 10 °C 2: 81 percent / ethanol / 24 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: ammonia 2: ethanol / Reflux View Scheme |
2-methoxyethyl-3-oxobutanoate
nimodipin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77.5 percent / hydrogen chloride / toluene / 20 h / 10 °C 2: 81 percent / ethanol / 24 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: ammonium hydroxide 2: piperidine / propionic acid / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: piperidine; acetic acid 2: ethanol / Reflux View Scheme |
nimodipin
Conditions | Yield |
---|---|
With sodium In 2-methoxy-ethanol; water |
nimodipin
Conditions | Yield |
---|---|
With sodium In 2-methoxy-ethanol; water |
3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester
nimodipin
Conditions | Yield |
---|---|
With piperidine In propionic acid Reflux; Inert atmosphere; |
isopropyl 3-aminocrotonate
(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate
nimodipin
Conditions | Yield |
---|---|
In ethanol Reflux; |
nimodipin
3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 2844.3 Torr; for 2h; | 95% |
With hydrogen In tetrahydrofuran; water at 120℃; under 37503.8 Torr; for 17h; chemoselective reaction; | 95% |
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 6h; Solvent; Inert atmosphere; Green chemistry; chemoselective reaction; | 90% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Cooling with ice; | 95% |
Stage #1: nimodipin With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: carbonochloridic acid, chloromethyl ester In tetrahydrofuran at 20℃; | 94.84% |
nimodipin
Conditions | Yield |
---|---|
With TFA-d; water-d2 In 1-methyl-pyrrolidin-2-one at 50℃; for 24h; Schlenk technique; Inert atmosphere; | 94% |
nimodipin
Nimodipine Oxidized
Conditions | Yield |
---|---|
With potassium carbonate; eosin Y bis(tetrabutyl ammonium salt) In methanol; water at 20℃; for 12h; Irradiation; Green chemistry; | 78% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 12h; | 78.4% |
With nitric acid at 100℃; for 1h; | 71% |
formaldehyd
nimodipin
Conditions | Yield |
---|---|
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 30h; | 77% |
With sodium carbonate In water; dimethyl sulfoxide at 130℃; for 15h; Schlenk technique; Sealed tube; Green chemistry; | 48% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; | 55% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at -40 - 20℃; | 52.7% |
nimodipin
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at 37℃; for 6h; pH=3 - 3.5; | 45% |
nimodipin
2,6-Dimethyl-4-(4-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester
Conditions | Yield |
---|---|
In ethanol; water for 60h; Irradiation; |
Conditions | Yield |
---|---|
With α1-acid glycoprotein HPLC column resolution of racemate; | |
With Chiralpak IC In hexane; isopropyl alcohol Reagent/catalyst; Solvent; Resolution of racemate; | |
With trifluoroacetic acid In methanol; isopropyl alcohol at 35℃; under 103432 Torr; Reagent/catalyst; Resolution of racemate; Supercritical conditions; |
Conditions | Yield |
---|---|
In ethanol at 37℃; for 2h; pH=7.4; Kinetics; Further Variations:; Reaction partners; Solvents; |
Conditions | Yield |
---|---|
With Britton-Robinson buffer In water; N,N-dimethyl-formamide at 37℃; pH=7.4; Kinetics; |
Conditions | Yield |
---|---|
In methanol Quantum yield; Product distribution; Further Variations:; Solvents; wavelengths; presence of air; Irradiation; |
nimodipin
B
2-Methoxyethyl 1-Methylethyl 1,4-Dihydro-2,6-dimethyl-4-(3-hydroxylaminophenyl)-3,5-pyridinedicarboxylate
C
Nimodipine Oxidized
D
3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile Quantum yield; Irradiation; |
Conditions | Yield |
---|---|
In acetic acid | |
In acetic acid |
nimodipin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 5 h / 55 - 60 °C 3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 5 h / 20 °C View Scheme |
nimodipin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 55 - 60 °C 3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 2 h / 20 °C View Scheme |
nimodipin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 4 h / 55 - 60 °C 3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 2 h / 20 °C View Scheme |
nimodipin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 50 - 60 °C 3: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 4 h / 20 °C View Scheme |
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