Nilvadipine supplier | CasNO.75530-68-6

Name
Nilvadipine
EINECS 805-887-5
CAS No. 75530-68-6
Article Data11
CAS DataBase
Density 1.32 g/cm³
Solubility
Melting Point 148-150 °C
Formula C₁₉H₁₉N₃O₆
Boiling Point 526.7 °C at 760 mmHg
Molecular Weight 385.376
Flash Point 272.3 °C
Transport Information
Appearance yellow prisms
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms CL 287389;Escor;FK 235;FR 34235;Nivadil;Nivadip;SKF 102362;dl-Nilvadipine;
PSA 134.24000
LogP 3.30988

Synthetic route

: 1452166-70-9
isopropyl 2-hydroxyiminomethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 10 - 50℃; for 5h;	85.1%

: 186581-53-3, 908094-01-9
diazomethane

: sodium 2-cyano-5-isopropoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

A: 75530-68-6
nilvadipine

B: 145220-80-0
isopropyl 2-carbamoyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1, 4-dihydropyridine-5-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride 1.) AcOEt, 2.) AcOEt, ether; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 75530-60-8
isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate; acetic anhydride 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / water; methanol / 4 h / 20 °C 2: acetic anhydride; potassium carbonate / dimethyl sulfoxide / 5 h / 10 - 50 °C View Scheme

: 39562-25-9
3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester

: 4-Amino-3-imino-butyric acid methyl ester; compound with acetic acid

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
With sodium methylate In isopropyl alcohol Heating;

: 542-08-5
isopropyl acetoacetate

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / piperidinium acetate / propan-2-ol / 10 h / 45 - 55 °C 2: sodium methoxide / propan-2-ol / Heating View Scheme

: 99-61-6
3-nitro-benzaldehyde

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / piperidinium acetate / propan-2-ol / 10 h / 45 - 55 °C 2: sodium methoxide / propan-2-ol / Heating View Scheme

: 60705-25-1
4,4-dimethoxy-3-oxo-butyric acid methyl ester

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: piperidine / benzene / 3 h / Heating 2: 51.1 percent / 8.5 h / 95 - 120 °C 3: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature 4: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h View Scheme

: 14205-46-0
isopropyl 3-aminocrotonate

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 51.1 percent / 8.5 h / 95 - 120 °C 2: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature 3: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h View Scheme

: 99-61-6
3-nitro-benzaldehyde

platinum black: platinum black

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: piperidine / benzene / 3 h / Heating 2: 51.1 percent / 8.5 h / 95 - 120 °C 3: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature 4: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h View Scheme

: 67448-15-1
(E,Z)-methyl 4,4-dimethoxy-2-(3-nitrobenzylidene)acetoacetate

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 51.1 percent / 8.5 h / 95 - 120 °C 2: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature 3: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h View Scheme

: 75530-94-8
isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature 2: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h View Scheme

: 113201-61-9
2-cyano-1,4-dihydro-3-methoxycarbonyl-6-methyl-4-m-nitrophenylpyridine-5-carboxylic acid

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
With phosphorus pentachloride
With phosphorus pentachloride

: 497-19-8
sodium carbonate

: 113201-61-9
2-cyano-1,4-dihydro-3-methoxycarbonyl-6-methyl-4-m-nitrophenylpyridine-5-carboxylic acid

: 75530-68-6
nilvadipine

Conditions

Conditions	Yield
With phosphorus pentachloride In dichloromethane; ethyl acetate; benzene

: 75530-68-6
nilvadipine

: 99935-62-3
isopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Conditions

Conditions	Yield
With nitric acid; acetic acid for 3h; Ambient temperature;	93.8%

: 75530-68-6
nilvadipine

: 145220-80-0
isopropyl 2-carbamoyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1, 4-dihydropyridine-5-carboxylate

Conditions

Conditions	Yield
With sulfuric acid for 0.166667h;	87.9%

: 75530-68-6
nilvadipine

: 2-cyano-5-isopropoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Conditions

Conditions	Yield
With lithium iodide In pyridine for 6h; Heating;

: 811-98-3
d(4)-methanol

: 75530-68-6
nilvadipine

: trideuteriomethyl 2-cyano-5-isopropoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

Conditions

Conditions	Yield
With pyridine; 2-bromo-1-methyl-pyridinium iodide; N,N-dimethyl-aniline; lithium iodide 1.) 110 deg C, 8 h, 2.) DMF, RT, 7.5 h; Yield given. Multistep reaction;

: 75530-68-6
nilvadipine

: 145220-88-8
methyl 2-cyano-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>pyridine-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C 3: 91.8 percent / p-TsOH / 1 h / Heating 4: 60.5 percent / p-TsOH / methanol / 15.5 h / Heating View Scheme

: 75530-68-6
nilvadipine

: 2-cyano-5-isopropoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: LiI / pyridine / 5 h / Heating View Scheme

: 75530-68-6
nilvadipine

: isopropyl 2-carbamoyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87.9 percent / 80percent aq. H2SO4 / 0.17 h 2: 79.8 percent / MnO2 / CHCl3 / 5 h / Ambient temperature View Scheme

: 75530-68-6
nilvadipine

: 145220-89-9
2-cyano-5-isopropoxycarbonyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-N-oxide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C View Scheme

: 75530-68-6
nilvadipine

: 145220-90-2
isopropyl 6-acetoxymethyl-2-cyano-3-methoxycarbonyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C 3: 91.8 percent / p-TsOH / 1 h / Heating View Scheme

: 75530-68-6
nilvadipine

: lithium 2-cyano-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>pyridine-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C 3: 91.8 percent / p-TsOH / 1 h / Heating 4: 60.5 percent / p-TsOH / methanol / 15.5 h / Heating 5: 38.2 percent / LiI / pyridine / 2.5 h / 100 °C View Scheme
Multi-step reaction with 5 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C 3: 91.8 percent / p-TsOH / 1 h / Heating 4: 86.4 percent / LiI / pyridine / 3 h / 100 °C 5: 13.7 percent / LiOH*H2O / methanol / 3 h / Heating View Scheme

: 75530-68-6
nilvadipine

: sodium 2-cyano-6-hydroxymethyl-3-methoxycarbonyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C 3: 91.8 percent / p-TsOH / 1 h / Heating 4: 60.5 percent / p-TsOH / methanol / 15.5 h / Heating 5: 74.6 percent / aq. NaHCO3 / methanol / 11 h / Heating View Scheme

: 75530-68-6
nilvadipine

: lithium 6-acetoxymethyl-2-cyano-5-isopropoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93.8 percent / aq. HNO3, AcOH / 3 h / Ambient temperature 2: 58.9 percent / 30percent aq. H2O2, AcOH / 312 h / 70 °C 3: 91.8 percent / p-TsOH / 1 h / Heating 4: 86.4 percent / LiI / pyridine / 3 h / 100 °C View Scheme

Nilvadipine Specification

The Nilvadipine, with the CAS registry number 75530-68-6, is also known as 5-Isopropyl 3-methyl 2-cyano-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate. It belongs to the product categories of Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C₁₉H₁₉N₃O₆ and molecular weight is 385.37. Its IUPAC name is called 3-O-methyl 5-O-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Physical properties of Nilvadipine: (1)ACD/LogP: 1.72; (2)ACD/LogD (pH 5.5): 1.72; (3)ACD/LogD (pH 7.4): 1.72; (4)ACD/BCF (pH 5.5): 12.03; (5)ACD/BCF (pH 7.4): 12.03; (6)ACD/KOC (pH 5.5): 206.47; (7)ACD/KOC (pH 7.4): 206.47; (8)#H bond acceptors: 9; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 7; (11)Index of Refraction: 1.584; (12)Molar Refractivity: 97.1 cm³; (13)Molar Volume: 290 cm³; (14)Surface Tension: 57 dyne/cm; (15)Density: 1.32 g/cm³; (16)Flash Point: 272.3 °C; (17)Enthalpy of Vaporization: 80.11 kJ/mol; (18)Boiling Point: 526.7 °C at 760 mmHg; (19)Vapour Pressure: 3.5E-11 mmHg at 25°C.

Preparation: this chemical can be prepared by 3-nitrobenzaldehyde, piperidine, 4,4 - dimethoxy methyl acetoacetate and acetic acid. This reaction will need 2-amino-2-crotonic acid isopropyl.

Uses of Nilvadipine: it is a calcium channel blocker (CCB) for the treatment of hypertension and chronic major cerebral artery occlusion. It can be used as an antihypertensive and antianginal. it can be used as calcium antagonists of dihydropyridine. Besides, it also can be used for essential hypertension. This chemical's classification codes are Antagonist [calcium channel]; Antihypertensive agents; Calcium channel blockers; Cardiovascular Agents; Drug / Therapeutic Agent; Membrane Transport Modulators; Reproductive Effect.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)C)\C1=C(\NC(/C#N)=C(/C(=O)OC)C1c2cccc([N+]([O-])=O)c2)C
(2)InChI: InChI=1/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3
(3)InChIKey: FAIIFDPAEUKBEP-UHFFFAOYAX

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	3850ug/kg (3.85mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
dog	LD50	oral	510mg/kg (510mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
mouse	LD50	intravenous	9150ug/kg (9.15mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
mouse	LD50	oral	1300mg/kg (1300mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
mouse	LD50	subcutaneous	> 320mg/kg (320mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat	LD50	intravenous	9650ug/kg (9.65mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat	LD50	oral	1560mg/kg (1560mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
rat	LD50	subcutaneous	> 1gm/kg (1000mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.

Product Name

Nilvadipine

Synthetic route

Nilvadipine Specification

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