Synthesis routes of Methyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoate

Methyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoate

カタログ番号 B8816364

分子量: 238.66 g/mol

InChIキー: MNMKWCPLHQYQLU-UHFFFAOYSA-N

注意: 研究専用です。人間または獣医用ではありません。

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Patent

US06603006B2

Procedure details

24.0 g (75.4 mmoles) of ethyl 3-amino-4-(2-(phthalimido)ethoxy)crotonate and 18.9 g (79.2 mmoles) of methyl 2-(2-chlorobenzylidene)acetoacetate in 64 ml of ethanol were heated under reflux for 20 hours. The reaction mixture was diluted with 56 ml of ethanol and was cooled to crystallise the product. 14.2 g (yield 70%) of 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(2-phthalimidoethoxy)methyl-1,4-dihydropyridine were obtained.

Name

ethyl 3-amino-4-(2-(phthalimido)ethoxy)crotonate

Quantity

24 g

Type

reactant

Reaction Step One

Name

methyl 2-(2-chlorobenzylidene)acetoacetate

Quantity

18.9 g

Type

reactant

Reaction Step One

Name

ethanol

Quantity

64 mL

Type

solvent

Reaction Step One

Name

ethanol

Quantity

56 mL

Type

solvent

Reaction Step Two

Name

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(2-phthalimidoethoxy)methyl-1,4-dihydropyridine

Yield

70%

Identifiers

REACTION_CXSMILES

[NH2:1]/[C:2](/[CH2:9][O:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH:27]=[C:28]([C:33]([CH3:35])=O)[C:29]([O:31][CH3:32])=[O:30]>C(O)C>[Cl:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH:27]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:33]([CH3:35])[NH:1][C:2]([CH2:9][O:10][CH2:11][CH2:12][N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])=[C:3]1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Inputs

Step One

Name	ethyl 3-amino-4-(2-(phthalimido)ethoxy)crotonate
Quantity	24 g
Type	reactant
Smiles	N\C(=C/C(=O)OCC)\COCCN1C(C=2C(C1=O)=CC=CC2)=O

Name	methyl 2-(2-chlorobenzylidene)acetoacetate
Quantity	18.9 g
Type	reactant
Smiles	ClC1=C(C=C(C(=O)OC)C(=O)C)C=CC=C1

Name	ethanol
Quantity	64 mL
Type	solvent
Smiles	C(C)O

Step Two

Name	ethanol
Quantity	56 mL
Type	solvent
Smiles	C(C)O

Conditions

Other

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

Workups

TEMPERATURE

Type	TEMPERATURE
Details	under reflux for 20 hours
Duration	20 h

TEMPERATURE

Type	TEMPERATURE
Details	was cooled

CUSTOM

Type	CUSTOM
Details	to crystallise the product

Outcomes

Product

Name	4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(2-phthalimidoethoxy)methyl-1,4-dihydropyridine
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

Measurements

Type	Value	Analysis
AMOUNT: MASS	14.2 g
YIELD: PERCENTYIELD	70%
YIELD: CALCULATEDPERCENTYIELD	34.9%

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.