Nifedipine
货号 B3420541
分子量: 346.3 g/mol
InChI 键: HYIMSNHJOBLJNT-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US05126457
Procedure details
Into a 1-liter glass reactor 60.4 g (0.4 mole) of 2-nitro-benzaldehyde, 102.1 g (0.88 mole) of methyl acetoacetate, 28.25 g (0.415 mole) of a 25% aqueous ammonium hydroxide solution and 150 ml of methanol are weighed in. The reactor is closed, whereupon the reaction mixture is heated to boiling at a temperature of 101°-103° C. and a pressure of 2.0-2.2 bar for 5 hours. The reaction mixture is cooled to 0°-5° C., the precipitated product is filtered and washed with methanol. Thus 110.5 g of nifedipine are obtained, yield 79.8%, m.p.: 171.5°-175° C.
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].[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[OH-:20].[NH4+:21]>CO>[CH3:16][C:14]1[NH:21][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH3:19])=[O:17])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:13]=1[C:12]([O:18][CH3:19])=[O:20] |f:2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
60.4 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=C(C=O)C=CC=C1
|
|
Name
|
|
|
Quantity
|
102.1 g
|
|
Type
|
reactant
|
|
Smiles
|
C(CC(=O)C)(=O)OC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[NH4+]
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The reactor is closed, whereupon the reaction mixture
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
is heated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to boiling at a temperature of 101°-103° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The reaction mixture is cooled to 0°-5° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the precipitated product is filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with methanol
|
Outcomes
Product
Details
Reaction Time |
5 h |
|
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 | 110.5 g | |
| YIELD: PERCENTYIELD | 79.8% |
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
Into a 1-liter glass reactor 60.4 g (0.4 mole) of 2-nitro-benzaldehyde, 102.1 g (0.88 mole) of methyl acetoacetate, 28.25 g (0.415 mole) of a 25% aqueous ammonium hydroxide solution and 150 ml of methanol are weighed in. The reactor is closed, whereupon the reaction mixture is heated to boiling at a temperature of 101°-103° C. and a pressure of 2.0-2.2 bar for 5 hours. The reaction mixture is cooled to 0°-5° C., the precipitated product is filtered and washed with methanol. Thus 110.5 g of nifedipine are obtained, yield 79.8%, m.p.: 171.5°-175° C.
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].[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[OH-:20].[NH4+:21]>CO>[CH3:16][C:14]1[NH:21][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH3:19])=[O:17])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:13]=1[C:12]([O:18][CH3:19])=[O:20] |f:2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
60.4 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=C(C=O)C=CC=C1
|
|
Name
|
|
|
Quantity
|
102.1 g
|
|
Type
|
reactant
|
|
Smiles
|
C(CC(=O)C)(=O)OC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[NH4+]
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The reactor is closed, whereupon the reaction mixture
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
is heated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to boiling at a temperature of 101°-103° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The reaction mixture is cooled to 0°-5° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the precipitated product is filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with methanol
|
Outcomes
Product
Details
Reaction Time |
5 h |
|
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 | 110.5 g | |
| YIELD: PERCENTYIELD | 79.8% |
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. |
