3-Nitrobenzaldehyde → HCID 86749798, compound

HRID 742290Notes

Reaction equation

HRID 742290 reaction equation
[C:1]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:12]/[C:13](/[CH3:19])=[CH:14]\[C:15]([O:17][CH3:18])=[O:16].[N+:20]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)([O-:22])=[O:21]>CC(O)C>[CH3:5][C:3]1[NH:12][C:13]([CH3:19])=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:26]([C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 11576Butyl acetoacetateHCID 643918Methyl 3-aminocrotonate

Product 1

HCID 86749798HCID 86749798, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of n-butyl acetoacetate (0.10 mole), methyl 3-aminocrotonate (0.10 mole), 3-nitrobenzaldehyde (0.10 mole) and 150 mL of i-PrOH was refluxed overnight (18 h). The volatiles were removed in vacuo and the residue purified by flash chromatography (SiO2 : EtOAc/Hex) to furnish the product in 49% yield as low melting, yellow solid: mp 69°-70° C. Anal. Calcd for C20H24N2O6 : C, 61.85; H, 6.23; N, 7.21. Found: C, 62.02; H, 6.21; N, 6.95.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue purified by flash chromatography (SiO2 : EtOAc/Hex)
  3. customto furnish the product in 49% yield as low melting, yellow solid

Sources & evidence

ORD record
ord-7cbea35ca0cb4b64aec9fd3f9d3d3dce
Source dataset
uspto-grants-1996_09
Patent number
US05554621

Reaction notes

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