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molecular formula C16H17NO6 B031883 Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate CAS No. 88150-75-8

Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate

Cat. No. B031883
M. Wt: 319.31 g/mol
InChI Key: RIGKLAOKQFKWNN-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04661485

Procedure details

Methyl 3-aminocrotonate (72.2 g; 0.627M) and 2-chlorobenzaldehyde (88.1 g; 0.627M) were added to a solution of ethyl 4-(2-phthalimidoethoxy)acetoacetate (200 g; 0.627M) in isopropanol (1 liter) and the mixture was heated under reflux for 20 hours. The isopropanol was evaporated under reduced pressure and replaced by acetic acid (1 liter). After granulation at 10° the solid was collected and slurried in methanol (300 ml). The solid was collected by filtration and dried in vacuo at 50° to afford the title compound, yield 84.4 g, m.p. 146°-147°.
Quantity
72.2 g
Type
reactant
Reaction Step One
Quantity
88.1 g
Type
reactant
Reaction Step One
Quantity
200 g
Type
reactant
Reaction Step One
Quantity
1 L
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.[C:18]1(=[O:40])[N:22]([CH2:23][CH2:24][O:25][CH2:26][C:27](=O)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:21](=[O:35])[C:20]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:19]12>C(O)(C)C>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH3:8])[NH:1][C:27]([CH2:26][O:25][CH2:24][CH2:23][N:22]2[C:21](=[O:35])[C:20]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:19]3[C:18]2=[O:40])=[C:28]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Inputs

Step One
Name
Quantity
72.2 g
Type
reactant
Smiles
N\C(=C/C(=O)OC)\C
Name
Quantity
88.1 g
Type
reactant
Smiles
ClC1=C(C=O)C=CC=C1
Name
Quantity
200 g
Type
reactant
Smiles
C1(C=2C(C(N1CCOCC(CC(=O)OCC)=O)=O)=CC=CC2)=O
Name
Quantity
1 L
Type
solvent
Smiles
C(C)(C)O

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
the mixture was heated
TEMPERATURE
Type
TEMPERATURE
Details
under reflux for 20 hours
Duration
20 h
CUSTOM
Type
CUSTOM
Details
The isopropanol was evaporated under reduced pressure
CUSTOM
Type
CUSTOM
Details
After granulation at 10° the solid was collected
FILTRATION
Type
FILTRATION
Details
The solid was collected by filtration
CUSTOM
Type
CUSTOM
Details
dried in vacuo at 50°

Outcomes

Product
Name
Type
product
Smiles
ClC1=C(C=CC=C1)C1C(=C(NC(=C1C(=O)OC)C)COCCN1C(C=2C(C1=O)=CC=CC2)=O)C(=O)OCC

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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