3-Nitrobenzaldehyde → HCID 15078614, compound

HRID 1709361Notes

Reaction equation

HRID 1709361 reaction equation
[C:1]([O:7][CH2:8][CH2:9][S:10][C:11](=[O:13])[CH3:12])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].[NH2:25]/[C:26](/[CH3:35])=[CH:27]\[C:28]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[O:29].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[C:11]([S:10][CH2:9][CH2:8][O:7][C:1]([C:2]1[CH:20]([C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=2)[C:27]([C:28]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[O:29])=[C:26]([CH3:35])[NH:25][C:3]=1[CH3:5])=[O:6])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 3014295Piperidinium acetateHCID 10081624HCID 10081624, compoundHCID 18318308HCID 18318308, compound

Product 1

HCID 15078614HCID 15078614, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2.04 g of 2-acetylthioethyl acetoacetate, 1.51 g of 3-nitrobenzaldehyde, 1.49 g of methoxyethyl 3-aminocrotonate and 0.15 g of piperidinium acetate in 20 ml of 2-propanol was refluxed for 4 hours. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel column chromatography [eluent: ethyl acetate - hexane (1 : 3)]to give 1.54 g of the title compound. m.p. 136-138° C.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-9b0de8df6e1b4eefb0180ec24ce8c4ad
Source dataset
uspto-grants-1990_08
Patent number
US04948899

Reaction notes

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