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molecular formula H2O2Pd B041862 Palladium(2+);dihydroxide CAS No. 12135-22-7

Palladium(2+);dihydroxide

Cat. No. B041862
M. Wt: 142.5 g/mol
InChI Key: NXJCBFBQEVOTOW-UHFFFAOYSA-L
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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
Quantity
224 mg
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
10 mg
Type
catalyst
Reaction Step One

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
Quantity
224 mg
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
10 mg
Type
catalyst
Reaction Step One

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.
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