Nifedipine
カタログ番号 B3420541
分子量: 346.3 g/mol
InChIキー: HYIMSNHJOBLJNT-UHFFFAOYSA-N
注意: 研究専用です。人間または獣医用ではありません。
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
[Compound]
Name
( 7 )
Quantity
0 (± 1) mol
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
|
[Compound]
|
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
[Compound]
Name
( 7 )
Quantity
0 (± 1) mol
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
|
[Compound]
|
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. |
