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molecular formula C13H11N3O5 B194619 3-(4-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione CAS No. 827026-45-9

3-(4-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Cat. No. B194619
M. Wt: 289.24 g/mol
InChI Key: JKPJLYIGKKDZDT-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08877932B2

Procedure details

Into a 5.0 L 4 necked RB flask, charged 100.0 g of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione, 10.0 g of 10% Pd/C and 3200 ml of DMF under nitrogen atmosphere. Stirred the mass and raise the reaction mass temperature to 60 -65° C. Started the hydrogen gas bubbling into reaction mass at temperature 60-65° C. for 6 hours. The progress of the reaction is monitored by TLC. Cooled the mass to temperature 25to 30° C. Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere and wash with dimethylformamide; wet Pd/C is transferred into a polythene bag for recovery. Distilled off the above organic layer solvent completely under vacuum below 60° C. Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min. Filtered the solid and wash with 200 mL of ethyl acetate (Lot-II). Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min. Dried Weight of the compound is 78.0 g.
[Compound]
Name
4
Quantity
5 L
Type
reactant
Reaction Step One
Quantity
100 g
Type
reactant
Reaction Step One
Name
Quantity
10 g
Type
catalyst
Reaction Step One
Name
Quantity
3200 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13])([O-])=O.[H][H]>[Pd].CN(C=O)C>[CH:11]1[CH:10]=[C:9]2[C:8](=[O:13])[N:7]([CH:14]3[C:15](=[O:21])[NH:16][C:17](=[O:20])[CH2:18][CH2:19]3)[CH2:6][C:5]2=[C:4]([NH2:1])[CH:12]=1

Inputs

Step One
Name
4
Quantity
5 L
Type
reactant
Smiles
Name
Quantity
100 g
Type
reactant
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
Name
Quantity
10 g
Type
catalyst
Smiles
[Pd]
Name
Quantity
3200 mL
Type
solvent
Smiles
CN(C)C=O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H][H]

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
30 °C
Stirring
Type
CUSTOM
Details
Stirred the mass
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
raise the reaction mass temperature to 60 -65° C
CUSTOM
Type
CUSTOM
Details
bubbling into reaction mass at temperature 60-65° C. for 6 hours
Duration
6 h
FILTRATION
Type
FILTRATION
Details
Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere
WASH
Type
WASH
Details
wash with dimethylformamide
DISTILLATION
Type
DISTILLATION
Details
Distilled off the above organic layer solvent completely under vacuum below 60° C
STIRRING
Type
STIRRING
Details
Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min
Duration
60 min
FILTRATION
Type
FILTRATION
Details
Filtered the solid
WASH
Type
WASH
Details
wash with 200 mL of ethyl acetate (Lot-II)
CUSTOM
Type
CUSTOM
Details
Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min
Duration
150 (± 30) min

Outcomes

Product
Name
Type
Smiles
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O

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
US08877932B2

Procedure details

Into a 5.0 L 4 necked RB flask, charged 100.0 g of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione, 10.0 g of 10% Pd/C and 3200 ml of DMF under nitrogen atmosphere. Stirred the mass and raise the reaction mass temperature to 60 -65° C. Started the hydrogen gas bubbling into reaction mass at temperature 60-65° C. for 6 hours. The progress of the reaction is monitored by TLC. Cooled the mass to temperature 25to 30° C. Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere and wash with dimethylformamide; wet Pd/C is transferred into a polythene bag for recovery. Distilled off the above organic layer solvent completely under vacuum below 60° C. Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min. Filtered the solid and wash with 200 mL of ethyl acetate (Lot-II). Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min. Dried Weight of the compound is 78.0 g.
[Compound]
Name
4
Quantity
5 L
Type
reactant
Reaction Step One
Quantity
100 g
Type
reactant
Reaction Step One
Name
Quantity
10 g
Type
catalyst
Reaction Step One
Name
Quantity
3200 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13])([O-])=O.[H][H]>[Pd].CN(C=O)C>[CH:11]1[CH:10]=[C:9]2[C:8](=[O:13])[N:7]([CH:14]3[C:15](=[O:21])[NH:16][C:17](=[O:20])[CH2:18][CH2:19]3)[CH2:6][C:5]2=[C:4]([NH2:1])[CH:12]=1

Inputs

Step One
Name
4
Quantity
5 L
Type
reactant
Smiles
Name
Quantity
100 g
Type
reactant
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
Name
Quantity
10 g
Type
catalyst
Smiles
[Pd]
Name
Quantity
3200 mL
Type
solvent
Smiles
CN(C)C=O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H][H]

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
30 °C
Stirring
Type
CUSTOM
Details
Stirred the mass
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
raise the reaction mass temperature to 60 -65° C
CUSTOM
Type
CUSTOM
Details
bubbling into reaction mass at temperature 60-65° C. for 6 hours
Duration
6 h
FILTRATION
Type
FILTRATION
Details
Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere
WASH
Type
WASH
Details
wash with dimethylformamide
DISTILLATION
Type
DISTILLATION
Details
Distilled off the above organic layer solvent completely under vacuum below 60° C
STIRRING
Type
STIRRING
Details
Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min
Duration
60 min
FILTRATION
Type
FILTRATION
Details
Filtered the solid
WASH
Type
WASH
Details
wash with 200 mL of ethyl acetate (Lot-II)
CUSTOM
Type
CUSTOM
Details
Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min
Duration
150 (± 30) min

Outcomes

Product
Name
Type
Smiles
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O

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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