4-Nitrobenzaldehyde → HCID 59550635, compound

HRID 1169580Notes

Reaction equation

HRID 1169580 reaction equation
C([O-])(=O)C.[NH4+:5].[C:6]([CH2:8][C:9]([O:11]CC)=O)#[N:7].[CH2:14]([O:16][C:17]([C:19]1([C:22](=O)[CH3:23])[CH2:21][CH2:20]1)=[O:18])[CH3:15].[N+:25]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([O-:27])=[O:26]>>[CH2:14]([O:16][C:17]([C:19]1([C:22]2[NH:5][C:9](=[O:11])[C:8]([C:6]#[N:7])=[C:32]([C:31]3[CH:34]=[CH:35][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=3)[CH:23]=2)[CH2:21][CH2:20]1)=[O:18])[CH3:15]

Participants

5

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 7764Ethyl cyanoacetateHCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateHCID 517165Ammonium Acetate

Product 1

HCID 59550635HCID 59550635, compoundYield 43.4%

Procedure

In analogy to GP 1, reaction of 28.9 g ammonium acetate (375 mmol, 8 eq.), 5 ml ethyl cyanoacetate (47.3 mmol, 1 eq.), 7.32 g 1-acetyl-cyclopropanecarboxylic acid ethyl ester (47 mmol, 1 eq.), and 7.08 g 4-nitrobenzaldehyde (47 mmol, 1 eq.) yielded 7.2 g product (43% yield).

Sources & evidence

ORD record
ord-618bf7a24ccb4877b66cc7b85a5d3f06
Source dataset
uspto-grants-2010_11
Patent number
US07825114B2

Reaction notes

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