Reaction #1256764

ord-4858a4a56c5f4c41958e192569a3c4ff

Reaction equation

CC(=O)[O-].[NH4+]
ammonium acetate
CCOC(=O)CC#N
ethyl cyanoacetate
CCOC(=O)C1(C(C)=O)CC1
1-acetyl-cyclopropanecarboxylic acid ethyl ester
O=Cc1cccc([N+](=O)[O-])c1
3-nitrobenzaldehyde
→
CCOC(=O)C1(c2cc(-c3cccc([N+](=O)[O-])c3)c(C#N)c(=O)[nH]2)CC1
product
Yield 10.0%
CCOC(=O)C1(c2cc(-c3cccc([N+](=O)[O-])c3)c(C#N)c(=O)[nH]2)CC1
1-[5-Cyano-4-(3-nitro-phenyl)-6-oxo-1,6-dihydro-pyridin-2-yl]-cyclopropanecarboxylic acid ethyl ester
Yield 10.0%

Reactants

CC(=O)[O-].[NH4+]
ammonium acetate
CCOC(=O)CC#N
ethyl cyanoacetate
CCOC(=O)C1(C(C)=O)CC1
1-acetyl-cyclopropanecarboxylic acid ethyl ester
O=Cc1cccc([N+](=O)[O-])c1
3-nitrobenzaldehyde

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

In analogy to GP 1, reaction of 30.8 g ammonium acetate (400 mmol), 11.3 g ethyl cyanoacetate (100 mmol), 15.6 g 1-acetyl-cyclopropanecarboxylic acid ethyl ester (100 mmol), and 15.1 g 3-nitrobenzaldehyde (100 mmol) yielded 3.5 g product (10% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07825114B2uspto-grants-2010_11