Benzene → HCID 70467484, compound

HRID 1731870Notes

Reaction equation

HRID 1731870 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.C([CH:16](C([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25]C=1)=O)[C:17]([OH:19])=[O:18])(O)=O.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[OH2:35].[CH:36]1[CH:41]=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[CH:41][C:36]([NH:29][C:34]1[C:16](=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:17]([O-:19])=[O:18])=[O:35].[NH2+:22]1[CH2:23][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 8082PiperidineHCID 8419VeratraldehydeHCID 20222317HCID 20222317, compound

Product 1

HCID 70467484HCID 70467484, compoundYield 95.8%

Procedure

A solution of 8.4 g of 3,4-dimethoxybenzaldehyde, 11.4 g of 2-carboxymalonanilic acid, and 4.3 g of piperidine in 50 ml of benzene is heated under reflux for 3 hours with the removal of water as formed during the reaction period. After the completion of the reaction, the reaction mixture is cooled and the precipitated crystals are collected by filtration and dried to obtain 19.7 g of piperidinium N-(3,4-dimethoxycinnamoyl)anthranilate (95.8% yield), m.p. 154°-156° C. The compound structure is confirmed by elemental analysis, and by IR and NMR spectroscopy.

Workup

  1. customas formed during the reaction period
  2. customAfter the completion of the reaction
  3. temperaturethe reaction mixture is cooled
  4. filtrationthe precipitated crystals are collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-6aeb4923f21648b2a38954da26d17e09
Source dataset
uspto-grants-1986_11
Patent number
US04623724

Reaction notes

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