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556815

Sigma-Aldrich

3-Ethyl-4-methyl-3-pyrrolin-2-one

97%

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About This Item

Empirical Formula (Hill Notation):
C7H11NO
CAS Number:
Molecular Weight:
125.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

mp

100-104 °C (lit.)

SMILES string

CCC1=C(C)CNC1=O

InChI

1S/C7H11NO/c1-3-6-5(2)4-8-7(6)9/h3-4H2,1-2H3,(H,8,9)

InChI key

YCTNTSVMJWIYTQ-UHFFFAOYSA-N

General description

3-Ethyl-4-methyl-3-pyrrolin-2-one, a five-membered α,β-unsaturated lactam derivative, has various applications in medicinal chemistry. It can be synthesized by employing following as starting materials:
  • allylamine, via palladium(II)-assisted cyclization
  • 4-methoxybenzylamine, via a ring-closing-metathesis strategy
  • 3-ethyl-1-(4-methoxybenzyl)-4-methyl-1,5-dihydro-2H-pyrrol-2- one

Application

3-Ethyl-4-methyl-3-pyrrolin-2-one (3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one) may be employed as a precursor for the synthesis of glimepiride (antidiabetic drug) and its derivatives (sulfonylurea drugs). It may also be employed for the preparation of 2-ethyl-3-methyl-(10H)-
dipyrrin-1-one.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Molecular recognition studies with a simple dipyrrinone.
Huggins MT, et al.
Tetrahedron, 63(52), 12994-12999 (2007)
Synthesis of 3-Ethyl-4-methyl-1, 5-dihydro-2H-pyrrol-2-one by Novel Palladium (II)-Catalyzed Cyclization and Ring-Closing Metathesis.
Chavan SP, et al.
Synthesis, 47(07), 955-960 (2015)

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