3-Nitrobenzaldehyde → HCID 15718253, compound

HRID 2107961Notes

Reaction equation

HRID 2107961 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][C:20]([CH3:31])([CH3:30])[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH:28]=[O:29])[CH2:24][CH2:23]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:32]/[C:33](/[CH3:39])=[CH:34]\[C:35]([O:37][CH3:38])=[O:36]>C(O)(C)C>[CH3:16][C:14]1[NH:32][C:33]([CH3:39])=[C:34]([C:35]([O:37][CH3:38])=[O:36])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][C:20]([CH3:31])([CH3:30])[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH:28]=[O:29])[CH2:24][CH2:23]1)=[O:17]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 15718279HCID 15718279, compound

Product 1

HCID 15718253HCID 15718253, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

425 mg of m-nitrobenzaldehyde, 830 mg of 3-(4-formyl-1-piperazinyl)-2,2-dimethylpropyl acetoacetate, and 324 mg of methyl 3-aminocrotonate were dissolved in 6 ml of isopropanol, and the solution was subjected to heating reflux for 12 hours. Then, the solvent was concentrated under reduced pressure. The residue was purified by the chromatography method [30 g silica gel, eluted with ethyl acetate) to give 1090 mg of the subject compound (yield: 75%). The IR and NMR data of the compound thus obtained are as follows: ##STR15##

Workup

  1. temperatureto heating
  2. temperaturereflux for 12 hours
  3. concentrationThen, the solvent was concentrated under reduced pressure
  4. customThe residue was purified by the chromatography method [30 g silica gel
  5. washeluted with ethyl acetate)

Sources & evidence

ORD record
ord-616666a90f9b410aa121592fc6b70b88
Source dataset
uspto-grants-1990_06
Patent number
US04937242

Reaction notes

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