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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

By catalytic hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione in solvents such as dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. under pressure or bubbling of hydrogen gas at atmospheric pressure, then filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I is obtained. The polymorphic form-I of Lenalidomide can also be obtained by transfer hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione using solvents dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. using ammonium formate or formic acid as source of hydrogen. The precious metal catalysts used in the hydrogenation are Raney Nickel, palladium etc., followed by filteration of catalyst and distillation of the solvent under high vacuum.
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
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Reaction Step One
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solvent
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reactant
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Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
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-:3])=[O:2].CN(C)C=O>C(O)(C)C.C(O)C.CO>[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.[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-:3])=[O:2]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
Name
Quantity
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Type
reactant
Smiles
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0 (± 1) mol
Type
solvent
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
bubbling of hydrogen gas at atmospheric pressure
DISTILLATION
Type
DISTILLATION
Details
filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I
CUSTOM
Type
CUSTOM
Details
is obtained

Outcomes

Product
Name
Type
product
Smiles
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O
Name
Type
product
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=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

By catalytic hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione in solvents such as dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. under pressure or bubbling of hydrogen gas at atmospheric pressure, then filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I is obtained. The polymorphic form-I of Lenalidomide can also be obtained by transfer hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione using solvents dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. using ammonium formate or formic acid as source of hydrogen. The precious metal catalysts used in the hydrogenation are Raney Nickel, palladium etc., followed by filteration of catalyst and distillation of the solvent under high vacuum.
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
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0 (± 1) mol
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solvent
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reactant
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Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
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-:3])=[O:2].CN(C)C=O>C(O)(C)C.C(O)C.CO>[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.[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-:3])=[O:2]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN(C=O)C
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
bubbling of hydrogen gas at atmospheric pressure
DISTILLATION
Type
DISTILLATION
Details
filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I
CUSTOM
Type
CUSTOM
Details
is obtained

Outcomes

Product
Name
Type
product
Smiles
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O
Name
Type
product
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=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

By catalytic hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione in solvents such as dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. under pressure or bubbling of hydrogen gas at atmospheric pressure, then filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I is obtained. The polymorphic form-I of Lenalidomide can also be obtained by transfer hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione using solvents dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. using ammonium formate or formic acid as source of hydrogen. The precious metal catalysts used in the hydrogenation are Raney Nickel, palladium etc., followed by filteration of catalyst and distillation of the solvent under high vacuum.
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
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Type
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Reaction Step Two
Quantity
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Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
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-:3])=[O:2].CN(C)C=O>C(O)(C)C.C(O)C.CO>[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.[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-:3])=[O:2]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN(C=O)C
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
bubbling of hydrogen gas at atmospheric pressure
DISTILLATION
Type
DISTILLATION
Details
filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I
CUSTOM
Type
CUSTOM
Details
is obtained

Outcomes

Product
Name
Type
product
Smiles
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O
Name
Type
product
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=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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