Benzene → HCID 70403490, compound

HRID 2119163Notes

Reaction equation

HRID 2119163 reaction equation
[CH3:1][CH2:2][C:3](=[O:11])[CH2:4][C:5]([O:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[N+:12]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1C=O)([O-:14])=[O:13].N1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[CH:29]1C=CC=C[CH:30]=1>>[CH3:1][CH2:2][C:3](=[O:11])[CH2:4][C:5]([O:7][C:8]1([C:22]2[CH:21]=[CH:20][CH:19]=[CH:16][C:15]=2[N+:12]([O-:14])=[O:13])[CH2:10][C:9]1=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:6]

Participants

5

Reactant 4

HCID 241BenzeneHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 70402746HCID 70402746, compound

Product 1

HCID 70403490HCID 70403490, compoundYield 49%

Procedure

8.2 g (52.6 millimole) of Cyclopropyl methylacetoacetate and 6.6 g (43.8 millimole) of orthonitrobenzaldehyde were dissolved in 55 ml of benzene and 0.44 ml (4.38 millimole) of piperidine was added to the solution and it was dehydrated by refluxing for 15 hrs in a Dean-Stark apparatus. After removing the solvent and base under reduced pressure, the residue was purified on silica gel by chromatography to obtain 6.14 g (49%) of title product.

Workup

  1. temperatureby refluxing for 15 hrs in a Dean-Stark apparatus
  2. customAfter removing the solvent and base under reduced pressure
  3. customthe residue was purified on silica gel by chromatography

Sources & evidence

ORD record
ord-7be238ab2cae49f69902309ccf36de16
Source dataset
uspto-grants-1987_07
Patent number
US04683234

Reaction notes

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