Palladium(2+);dihydroxide
Numéro de catalogue B041862
Poids moléculaire: 142.5 g/mol
Clé InChI: NXJCBFBQEVOTOW-UHFFFAOYSA-L
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
US05723618
Procedure details
A mixture of 4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IBa, 150 mg), palladium hydroxide on carbon (10 mg) and ammonium formate (224 mg) in methanol (10 mL) was refluxed for 5 h under a nitrogen atmosphere. On cooling to room temperature, the mixture was filtered through a pad of celite. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a solvent mixture of dichloromethane and methanol (9:1; 100 mL), and dichloromethane, methanol and ammonium hydroxide (90:10:1; 500 mL) as eluent afforded the title compound (IAa 88 mg).
Name
4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
Quantity
150 mg
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH2:12][O:13][CH2:14][CH:15]=[N:16]O)[NH:9][C:10]=1[CH3:11])=[O:4].C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH2:12][O:13][CH2:14][CH2:15][NH2:16])[NH:9][C:10]=1[CH3:11])=[O:4] |f:1.2,4.5.6|
|
Inputs
Step One
|
Name
|
4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
|
|
Quantity
|
150 mg
|
|
Type
|
reactant
|
|
Smiles
|
COC(=O)C=1C(C(=C(NC1C)COCC=NO)C(=O)OCC)C1=C(C=CC=C1)Cl
|
|
Name
|
|
|
Quantity
|
224 mg
|
|
Type
|
reactant
|
|
Smiles
|
C(=O)[O-].[NH4+]
|
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
|
Name
|
|
|
Quantity
|
10 mg
|
|
Type
|
catalyst
|
|
Smiles
|
[OH-].[OH-].[Pd+2]
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
was refluxed for 5 h under a nitrogen atmosphere
|
|
Duration
|
5 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the mixture was filtered through a pad of celite
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The filtrate was concentrated in vacuo
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Purification of the residue by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
a solvent mixture of dichloromethane and methanol (9:1; 100 mL), and dichloromethane, methanol and ammonium hydroxide (90:10:1; 500 mL) as eluent
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
COC(=O)C=1C(C(=C(NC1C)COCCN)C(=O)OCC)C1=C(C=CC=C1)Cl
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 88 mg | |
| YIELD: CALCULATEDPERCENTYIELD | 60.7% |
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
US05723618
Procedure details
A mixture of 4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IBa, 150 mg), palladium hydroxide on carbon (10 mg) and ammonium formate (224 mg) in methanol (10 mL) was refluxed for 5 h under a nitrogen atmosphere. On cooling to room temperature, the mixture was filtered through a pad of celite. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a solvent mixture of dichloromethane and methanol (9:1; 100 mL), and dichloromethane, methanol and ammonium hydroxide (90:10:1; 500 mL) as eluent afforded the title compound (IAa 88 mg).
Name
4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
Quantity
150 mg
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH2:12][O:13][CH2:14][CH:15]=[N:16]O)[NH:9][C:10]=1[CH3:11])=[O:4].C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH2:12][O:13][CH2:14][CH2:15][NH2:16])[NH:9][C:10]=1[CH3:11])=[O:4] |f:1.2,4.5.6|
|
Inputs
Step One
|
Name
|
4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
|
|
Quantity
|
150 mg
|
|
Type
|
reactant
|
|
Smiles
|
COC(=O)C=1C(C(=C(NC1C)COCC=NO)C(=O)OCC)C1=C(C=CC=C1)Cl
|
|
Name
|
|
|
Quantity
|
224 mg
|
|
Type
|
reactant
|
|
Smiles
|
C(=O)[O-].[NH4+]
|
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
|
Name
|
|
|
Quantity
|
10 mg
|
|
Type
|
catalyst
|
|
Smiles
|
[OH-].[OH-].[Pd+2]
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
was refluxed for 5 h under a nitrogen atmosphere
|
|
Duration
|
5 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the mixture was filtered through a pad of celite
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The filtrate was concentrated in vacuo
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Purification of the residue by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
a solvent mixture of dichloromethane and methanol (9:1; 100 mL), and dichloromethane, methanol and ammonium hydroxide (90:10:1; 500 mL) as eluent
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
COC(=O)C=1C(C(=C(NC1C)COCCN)C(=O)OCC)C1=C(C=CC=C1)Cl
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 88 mg | |
| YIELD: CALCULATEDPERCENTYIELD | 60.7% |
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. |
