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

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

Numéro de catalogue B031883

: 88150-75-8

Poids moléculaire: 319.31 g/mol

Clé InChI: RIGKLAOKQFKWNN-UHFFFAOYSA-N

Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.

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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°.

Name

Methyl 3-aminocrotonate

Quantity

72.2 g

Type

reactant

Reaction Step One

Name

2-chlorobenzaldehyde

Quantity

88.1 g

Type

reactant

Reaction Step One

Name

ethyl 4-(2-phthalimidoethoxy)acetoacetate

Quantity

200 g

Type

reactant

Reaction Step One

Name

isopropanol

Quantity

1 L

Type

solvent

Reaction Step One

Name

title compound

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	Methyl 3-aminocrotonate
Quantity	72.2 g
Type	reactant
Smiles	N\C(=C/C(=O)OC)\C

Name	2-chlorobenzaldehyde
Quantity	88.1 g
Type	reactant
Smiles	ClC1=C(C=O)C=CC=C1

Name	ethyl 4-(2-phthalimidoethoxy)acetoacetate
Quantity	200 g
Type	reactant
Smiles	C1(C=2C(C(N1CCOCC(CC(=O)OCC)=O)=O)=CC=CC2)=O

Name	isopropanol
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	title compound
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

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.