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molecular formula C17H18N2O6 B3420541 Nifedipine CAS No. 193689-82-6

Nifedipine

Cat. No. B3420541
M. Wt: 346.3 g/mol
InChI Key: HYIMSNHJOBLJNT-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05126457

Procedure details

One proceeds as described in Example 7 except that 0.4 mole of 2-nitro-benzaldehyde, 0.415 mole of a 25% aqueous ammonium hydroxide solution and 1.40 moles of methyl acetoacetate are used. Thus 112.1 g of nifedipine are obtained, yield 81%, m.p.: 172°-175° C. The product complies with the requirements of USP XXI without further purification.
Quantity
0.4 mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
1.4 mol
Type
reactant
Reaction Step Three
Yield
81%

Identifiers

REACTION_CXSMILES
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[OH-:12].[NH4+:13].[C:14]([O:20][CH3:21])(=[O:19])[CH2:15][C:16]([CH3:18])=O>>[CH3:18][C:16]1[NH:13][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH3:21])=[O:19])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:15]=1[C:14]([O:20][CH3:21])=[O:12] |f:1.2|

Inputs

Step One
Name
Quantity
0.4 mol
Type
reactant
Smiles
[N+](=O)([O-])C1=C(C=O)C=CC=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[NH4+]
Step Three
Name
Quantity
1.4 mol
Type
reactant
Smiles
C(CC(=O)C)(=O)OC

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Name
Type
product
Smiles
CC1=C(C(C(=C(N1)C)C(=O)OC)C=2C=CC=CC2[N+](=O)[O-])C(=O)OC
Measurements
Type Value Analysis
AMOUNT: MASS 112.1 g
YIELD: PERCENTYIELD 81%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US05126457

Procedure details

One proceeds as described in Example 7 except that 0.4 mole of 2-nitro-benzaldehyde, 0.415 mole of a 25% aqueous ammonium hydroxide solution and 1.40 moles of methyl acetoacetate are used. Thus 112.1 g of nifedipine are obtained, yield 81%, m.p.: 172°-175° C. The product complies with the requirements of USP XXI without further purification.
Quantity
0.4 mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
1.4 mol
Type
reactant
Reaction Step Three
Yield
81%

Identifiers

REACTION_CXSMILES
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[OH-:12].[NH4+:13].[C:14]([O:20][CH3:21])(=[O:19])[CH2:15][C:16]([CH3:18])=O>>[CH3:18][C:16]1[NH:13][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH3:21])=[O:19])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:15]=1[C:14]([O:20][CH3:21])=[O:12] |f:1.2|

Inputs

Step One
Name
Quantity
0.4 mol
Type
reactant
Smiles
[N+](=O)([O-])C1=C(C=O)C=CC=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[NH4+]
Step Three
Name
Quantity
1.4 mol
Type
reactant
Smiles
C(CC(=O)C)(=O)OC

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Name
Type
product
Smiles
CC1=C(C(C(=C(N1)C)C(=O)OC)C=2C=CC=CC2[N+](=O)[O-])C(=O)OC
Measurements
Type Value Analysis
AMOUNT: MASS 112.1 g
YIELD: PERCENTYIELD 81%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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