3-Nitrobenzaldehyde → HCID 86749798, compound

HRID 1682436Notes

Reaction equation

HRID 1682436 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.; 1H NMR (DMSO-d6) δ9.03 (s, 1H), 7.98 (m, 2H), 7.58 (m, 2H), 4.96 (s, 1H), 3.91 (m, 2H), 3,53 (s, 3H), 2.28 (s, 3H), 2.26 (s, 3H), 1.45 (p, 2H, J=6.6 Hz), 1.18 (m, 4H), and 0.83 (t, 3H, J=7.4 Hz); 13C NMR (DMSO-d6) δ167.0, 166.5, 150.1, 147.5, 146.5, 134.1, 129.7, 121.7, 121.1, 101.0, 100.9, 63.0, 50.8, 39.1, 30.2, 18.7, 18.3, and 13.5. 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-3e1e3c50f7e049d7bbd2b10b27ccb846
Source dataset
uspto-grants-1997_06
Patent number
US05635503

Reaction notes

Loading…