4-Nitrobenzaldehyde → HCID 23135183, compound

HRID 1713006Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[C:6]([CH2:8][C:9]([O:11]CC)=O)#[N:7].[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](=O)[CH3:17].[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)([O-:23])=[O:22]>>[C:15]([C:16]1[NH:5][C:9](=[O:11])[C:8]([C:6]#[N:7])=[C:28]([C:27]2[CH:30]=[CH:31][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)[CH:17]=1)([CH3:20])([CH3:19])[CH3:14]

Participants

Reactant 4

HCID 5414-Nitrobenzaldehyde

HCID 6416Pinacolone

HCID 7764Ethyl cyanoacetate

HCID 517165Ammonium Acetate

Product 1

HCID 23135183HCID 23135183, compoundYield 34%

Procedure

In analogy to GP 1, reaction of 61.7 g ammonium acetate (800 mmol, 8 eq.), 10.73 ml ethyl cyanoacetate (100 mmol, 1 eq.), 12.55 ml 3,3-dimethylbutan-2-one (100 mmol, 1 eq.), and 15.12 g 4-nitrobenzaldehyde (100 mmol, 1 eq.) yielded 10.02 g product (34% yield).

Sources & evidence

ORD record: ord-61cd500aea494328ac909641abf66f35
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795264B2

Reaction notes

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