4-Nitrobenzaldehyde → 2-(4-nitrobenzylidene)indan-1-one

HRID 378848Notes

Reaction equation

HRID 378848 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].N1CCCCC1>C(O)(=O)C>[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 67351-IndanoneHCID 8082Piperidine

Product 1

HCID 3672292-(4-nitrobenzylidene)indan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of indan-1-one (20.0 g), 4-nitrobenzaldehyde (27.0 g), glacial acetic acid (3.0 g) and piperidine (3.06 g) was heated at 95° C. under nitrogen for 3.5 h. The mixture was cooled to 20° C. and filtered to give a solid which was recrystallized from industrial methylated spirit to give 2-(4-nitrobenzylidene)indan-1-one.

Workup

  1. temperatureThe mixture was cooled to 20° C.
  2. filtrationfiltered
  3. customto give a solid which
  4. customwas recrystallized from industrial methylated spirit

Sources & evidence

ORD record
ord-63a04bd778a34b2981c62e0403cba958
Source dataset
uspto-grants-2001_10
Patent number
US06297238B1

Reaction notes

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