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molecular formula C12H15NO4 B1200448 4-[(4-methoxyphenyl)formamido]butanoic acid CAS No. 72432-14-5

4-[(4-methoxyphenyl)formamido]butanoic acid

Cat. No. B1200448
M. Wt: 237.25 g/mol
InChI Key: DZTVZKSCFQIBMV-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04369139

Procedure details

10 g. of phosphorus pentoxide and 6 ml. of orthophosphoric acid (at least 85%) are warmed with one another. 2.0 g. of 4-(p-methoxybenzoylamino)butyric acid are added at room temperature to the resulting solution. The mixture is warmed to 50° C. for 60 minutes, subsequently treated with ice and extracted with ethyl acetate. The organic phase is washed first with cold water, then with cold sodium bicarbonate solution and finally again with water and dried over sodium sulfate. The residue is triturated with diethyl ether and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120°-122° C.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[CH3:20][O:21][C:22]1[CH:36]=[CH:35][C:25]([C:26]([NH:28][CH2:29][CH2:30][CH2:31][C:32](O)=[O:33])=[O:27])=[CH:24][CH:23]=1>>[CH3:20][O:21][C:22]1[CH:36]=[CH:35][C:25]([C:26]([N:28]2[CH2:29][CH2:30][CH2:31][C:32]2=[O:33])=[O:27])=[CH:24][CH:23]=1

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
P(O)(O)(O)=O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC1=CC=C(C(=O)NCCCC(=O)O)C=C1

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
50 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
subsequently treated with ice
EXTRACTION
Type
EXTRACTION
Details
extracted with ethyl acetate
WASH
Type
WASH
Details
The organic phase is washed first with cold water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
with cold sodium bicarbonate solution and finally again with water and dried over sodium sulfate
CUSTOM
Type
CUSTOM
Details
The residue is triturated with diethyl ether

Outcomes

Product
Name
Type
product
Smiles
COC1=CC=C(C(=O)N2C(CCC2)=O)C=C1

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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