4-Nitrobenzaldehyde → HCID 59463728, compound

HRID 1713009Notes

Reaction equation

HRID 1713009 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](=[O:24])[C:18]([CH3:23])([CH3:22])[C:19](=O)[CH3:20])[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](=[O:24])[C:18]([C:19]1[NH:5][C:9](=[O:11])[C:8]([C:6]#[N:7])=[C:32]([C:31]2[CH:34]=[CH:35][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=2)[CH:20]=1)([CH3:23])[CH3:22])[CH3:15]

Participants

5

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 7764Ethyl cyanoacetateHCID 69002Ethyl 2,2-dimethylacetoacetateHCID 517165Ammonium Acetate

Product 1

HCID 59463728HCID 59463728, compoundYield 11.7%

Procedure

In analogy to GP 1, reaction of 1.85 g ammonium acetate (24 mmol, 8 eq.), 0.28 ml ethyl cyanoacetate (3 mmol, 1 eq.), 475 mg 2,2-dimethyl-3-oxo-butyric acid ethyl ester (3 mmol, 1 eq.), and 453 mg 4-nitrobenzaldehyde (3 mmol, 1 eq.) yielded 125 mg product (11% yield).

Sources & evidence

ORD record
ord-f087adb0906847639d836accb5a48e92
Source dataset
uspto-grants-2010_09
Patent number
US07795264B2

Reaction notes

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