4-Nitrobenzaldehyde → HCID 58751679, compound

HRID 1713007Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[C:6]([CH2:8][C:9]([O:11]CC)=O)#[N:7].[CH3:14][CH:15]([CH3:19])[C:16](=O)[CH3:17].[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)([O-:22])=[O:21]>>[CH:15]([C:16]1[NH:5][C:9](=[O:11])[C:8]([C:6]#[N:7])=[C:27]([C:26]2[CH:29]=[CH:30][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=2)[CH:17]=1)([CH3:19])[CH3:14]

Participants

Reactant 4

HCID 5414-Nitrobenzaldehyde

HCID 7764Ethyl cyanoacetate

HCID 112513-Methyl-2-butanone

HCID 517165Ammonium Acetate

Product 1

HCID 58751679HCID 58751679, compoundYield 15%

Procedure

In analogy to GP 1, reaction of 61.7 g ammonium acetate (800 mmol, 8 eq.), 10.67 ml ethyl cyanoacetate (100 mmol, 1 eq.), 10.71 ml 3-methyl-butan-2-one (100 mmol, 1 eq.), and 15.12 g 4-nitrobenzaldehyde (100 mmol, 1 eq.) yielded 4.24 g product (15% yield).

Sources & evidence

ORD record: ord-45ef1772763f4660ae8ee2411de069a1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795264B2

Reaction notes

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