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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
US04467093

Procedure details

2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.2 mole, 23.2 g) and NH4OH (12 ml) were heated in methanol (20 ml) in the presence of pyridine for several (7) hours. After cooling to 15° C. the precipitated product was filtered off. The crude product was crystallized from acetic acid to yield 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (21.7 g, 62% of the theory), m.p. 172°-174° C.
Name
2-Nitrobenzaldehyde diacetate
Quantity
25.4 g
Type
reactant
Reaction Step One
Quantity
23.2 g
Type
reactant
Reaction Step One
Name
Quantity
12 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
( 7 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
20 mL
Type
reactant
Reaction Step One

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].[CH3:12][C:13]([CH2:15][C:16]([OH:18])=[O:17])=O.[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.[NH4+:27].[OH-].N1C=CC=CC=1.[CH3:35]O>>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]1[C:15]([C:16]([O:18][CH3:35])=[O:17])=[C:13]([CH3:12])[NH:27][C:21]([CH3:23])=[C:20]1[C:19]([O:25][CH3:26])=[O:24])([O-:3])=[O:2] |f:0.1,3.4|

Inputs

Step One
Name
2-Nitrobenzaldehyde diacetate
Quantity
25.4 g
Type
reactant
Smiles
[N+](=O)([O-])C1=C(C=O)C=CC=C1.CC(=O)CC(=O)O
Name
Quantity
23.2 g
Type
reactant
Smiles
C(CC(=O)C)(=O)OC
Name
Quantity
12 mL
Type
reactant
Smiles
[NH4+].[OH-]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N1=CC=CC=C1
Name
( 7 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
20 mL
Type
reactant
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
was filtered off
CUSTOM
Type
CUSTOM
Details
The crude product was crystallized from acetic acid

Outcomes

Product
Name
Type
product
Smiles
[N+](=O)([O-])C1=C(C=CC=C1)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC

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
US04467093

Procedure details

2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.2 mole, 23.2 g) and NH4OH (12 ml) were heated in methanol (20 ml) in the presence of pyridine for several (7) hours. After cooling to 15° C. the precipitated product was filtered off. The crude product was crystallized from acetic acid to yield 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (21.7 g, 62% of the theory), m.p. 172°-174° C.
Name
2-Nitrobenzaldehyde diacetate
Quantity
25.4 g
Type
reactant
Reaction Step One
Quantity
23.2 g
Type
reactant
Reaction Step One
Name
Quantity
12 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
( 7 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
20 mL
Type
reactant
Reaction Step One

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].[CH3:12][C:13]([CH2:15][C:16]([OH:18])=[O:17])=O.[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.[NH4+:27].[OH-].N1C=CC=CC=1.[CH3:35]O>>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]1[C:15]([C:16]([O:18][CH3:35])=[O:17])=[C:13]([CH3:12])[NH:27][C:21]([CH3:23])=[C:20]1[C:19]([O:25][CH3:26])=[O:24])([O-:3])=[O:2] |f:0.1,3.4|

Inputs

Step One
Name
2-Nitrobenzaldehyde diacetate
Quantity
25.4 g
Type
reactant
Smiles
[N+](=O)([O-])C1=C(C=O)C=CC=C1.CC(=O)CC(=O)O
Name
Quantity
23.2 g
Type
reactant
Smiles
C(CC(=O)C)(=O)OC
Name
Quantity
12 mL
Type
reactant
Smiles
[NH4+].[OH-]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N1=CC=CC=C1
Name
( 7 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
20 mL
Type
reactant
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
was filtered off
CUSTOM
Type
CUSTOM
Details
The crude product was crystallized from acetic acid

Outcomes

Product
Name
Type
product
Smiles
[N+](=O)([O-])C1=C(C=CC=C1)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC

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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