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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
US09085530B2

Procedure details

To a mixture of 3-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-isoglutamine (9 g) in N,N-dimethylformamide (80 ml), was added thionyl chloride (6.6 g) by droplet below 0° C. for stirred reaction in heat preservation for 2˜3 hours. The resulting solution was added by droplet into mixture of ice and water and pH value was adjusted to 7˜8 with sodium carbonate. The mixture was stirred for 30 minutes and filtered to get light yellow crude. Refining with methanol gave 6.6 g of target yield as a light yellow solid. yield: 78%.
Name
3-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-isoglutamine
Quantity
9 g
Type
reactant
Reaction Step One
Quantity
80 mL
Type
solvent
Reaction Step One
Quantity
6.6 g
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five

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]([CH2:20][C:21](O)=O)[C@@H:15](C(=O)N)[NH2:16])[C:8]2=[O:13])([O-:3])=[O:2].S(Cl)(Cl)=O.[OH2:28].[C:29](=O)([O-])[O-:30].[Na+].[Na+]>CN(C)C=O.CO>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:20][CH2:21][C:29](=[O:30])[NH:16][C:15]1=[O:28])[C:8]2=[O:13])([O-:3])=[O:2] |f:3.4.5|

Inputs

Step One
Name
3-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-isoglutamine
Quantity
9 g
Type
reactant
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C([C@H](N)C(N)=O)CC(=O)O
Name
Quantity
80 mL
Type
solvent
Smiles
CN(C=O)C
Step Two
Name
Quantity
6.6 g
Type
reactant
Smiles
S(=O)(Cl)Cl
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Stirring
Type
CUSTOM
Details
for stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
by droplet below 0° C.
CUSTOM
Type
CUSTOM
Details
reaction in heat preservation for 2˜3 hours
STIRRING
Type
STIRRING
Details
The mixture was stirred for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
to get light yellow crude
CUSTOM
Type
CUSTOM
Details
yield as a light yellow solid

Outcomes

Product
Name
Type
Smiles
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 78%

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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