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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
US08946265B2

Procedure details

Triethylamine (140.8 g, 2.29 mol) was added at 25-30° C. to a solution of 3-amino-piperidine-2,6-dione hydrochloride (100 g, 0.61 mol) in N,N-dimethylformamide (800 ml). A solution of methyl 2-bromomethyl-3-nitro-benzoate (186.0 g, 1.13 mol) in acetonitrile (200 ml) was then added under stirring and a nitrogen atmosphere and the reaction mixture was heated to 50-55° C. for 8-10 hours. After completion of the reaction approximately 60% solvent was removed by distillation at 50-60° C. under reduced pressure (100 mbar). Water (1000 ml) was added to the residual mixture at 50-55° C. and stirred for 1 hour at this temperature. The resultant solid product was cooled to 25-30° C. and filtered. The solid was washed with water (500 ml) at 50-55° C., cooled at ambient temperature and filtered again. Finally the solid was washed with methanol (500 ml) at 50-55° C., cooled at 25-30° C. and filtered. The filtered solid product was dried at 50-55° C. under low pressure (200 mmHg) for 4 hours to give 3-(1-oxo-4-nitro-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione as a purple to ash coloured solid.
Quantity
140.8 g
Type
reactant
Reaction Step One
Quantity
100 g
Type
reactant
Reaction Step One
Quantity
800 mL
Type
solvent
Reaction Step One
Quantity
186 g
Type
reactant
Reaction Step Two
Quantity
200 mL
Type
solvent
Reaction Step Two
[Compound]
Name
solvent
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
C(N(CC)CC)C.Cl.[NH2:9][CH:10]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12][C:11]1=[O:17].Br[CH2:19][C:20]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:21]=1[C:22](OC)=[O:23]>CN(C)C=O.C(#N)C>[O:23]=[C:22]1[C:21]2[C:20](=[C:29]([N+:30]([O-:32])=[O:31])[CH:28]=[CH:27][CH:26]=2)[CH2:19][N:9]1[CH:10]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12][C:11]1=[O:17] |f:1.2|

Inputs

Step One
Name
Quantity
140.8 g
Type
reactant
Smiles
C(C)N(CC)CC
Name
Quantity
100 g
Type
reactant
Smiles
Cl.NC1C(NC(CC1)=O)=O
Name
Quantity
800 mL
Type
solvent
Smiles
CN(C=O)C
Step Two
Name
Quantity
186 g
Type
reactant
Smiles
BrCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]
Name
Quantity
200 mL
Type
solvent
Smiles
C(C)#N
Step Three
Name
solvent
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
52.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
under stirring
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
was removed by distillation at 50-60° C. under reduced pressure (100 mbar)
ADDITION
Type
ADDITION
Details
Water (1000 ml) was added to the residual mixture at 50-55° C.
STIRRING
Type
STIRRING
Details
stirred for 1 hour at this temperature
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
The resultant solid product was cooled to 25-30° C.
FILTRATION
Type
FILTRATION
Details
filtered
WASH
Type
WASH
Details
The solid was washed with water (500 ml) at 50-55° C.
TEMPERATURE
Type
TEMPERATURE
Details
cooled at ambient temperature
FILTRATION
Type
FILTRATION
Details
filtered again
WASH
Type
WASH
Details
Finally the solid was washed with methanol (500 ml) at 50-55° C.
TEMPERATURE
Type
TEMPERATURE
Details
cooled at 25-30° C.
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The filtered solid product was dried at 50-55° C. under low pressure (200 mmHg) for 4 hours
Duration
4 h

Outcomes

Product
Name
Type
product
Smiles
O=C1N(CC2=C(C=CC=C12)[N+](=O)[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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