Malonic Acid → 2-Nitro-5-piperazinylcinnamic acid

HRID 1649197Notes

Reaction equation

HRID 1649197 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][C:6]=1[CH:7]=O)([O-:4])=[O:3].N1CCCCC1.C(O)(=O)[CH2:26][C:27]([OH:29])=[O:28]>N1C=CC=CC=1>[N+:2]([C:5]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][C:6]=1[CH:7]=[CH:26][C:27]([OH:29])=[O:28])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 132363002-Nitro-5-piperazinylbenzaldehyde hydrochloride

Product 1

HCID 570123252-Nitro-5-piperazinylcinnamic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Nitro-5-piperazinylbenzaldehyde hydrochloride (47 g) was dissolved in 500 ml of pyridine and 5 g of piperidine and 100 g of malonic acid were added to the solution followed by heating under reflux for 5 hours. After cooling, crystals which formed were collected by filtration to give 42 g of 2-nitro-5-piperazinylcinnamic acid, m.p. 229°-237° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. customcrystals which formed
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-48eade3e6a474d77b242f2486351ebb8
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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