Water → HCID 70467484, compound

HRID 1731871Notes

Reaction equation

HRID 1731871 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].[C:36]1([CH3:42])C=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:42][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 962WaterHCID 1140TolueneHCID 8082PiperidineHCID 8419VeratraldehydeHCID 20222317HCID 20222317, compound

Product 1

HCID 70467484HCID 70467484, compoundYield 94.8%

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 toluene is heated for 3 hours under reflux with continuous removal of water 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 19.5 g of piperidinium N-(3,4-dimethoxycinnamoyl)anthranilate (94.8% yield), as confirmed by elemental analysis and spectroscopy.

Workup

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

Sources & evidence

ORD record
ord-756942962bbd4a399ecf5348ee63efd9
Source dataset
uspto-grants-1986_11
Patent number
US04623724

Reaction notes

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