4-Nitrobenzaldehyde → HCID 23135184, compound

HRID 2260998Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[C:6]([CH2:8][C:9]([O:11]C)=O)#[N:7].[CH:13]1([C:16](=O)[CH3:17])[CH2:15][CH2:14]1.[N+:19]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)([O-:21])=[O:20]>>[CH:13]1([C:16]2[NH:5][C:9](=[O:11])[C:8]([C:6]#[N:7])=[C:26]([C:25]3[CH:28]=[CH:29][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=3)[CH:17]=2)[CH2:15][CH2:14]1

Participants

Reactant 4

HCID 5414-Nitrobenzaldehyde

HCID 7747Methyl cyanoacetate

HCID 13004Cyclopropyl methyl ketone

HCID 517165Ammonium Acetate

Product 1

HCID 23135184HCID 23135184, compoundYield 35%

Procedure

In a modification of GP 1, reaction of 17.9 g ammonium acetate (233 mmol, 7 eq.), 3.5 ml methyl cyanoacetate (40 mmol, 1.2 eq.), 3.8 ml 1-cyclopropyl-ethanone (38 mmol, 1.15 eq.), and 5 g 4-nitrobenzaldehyde (33 mmol, 1 eq.) yielded 3.23 g product (11.5 mmol, 35% yield).

Sources & evidence

ORD record: ord-2ee7ac06066b4c228569091b3bb52a37
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846928B2

Reaction notes

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