Benzene → HCID 178420620, compound

HRID 1731872Notes

Reaction equation

HRID 1731872 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([CH:15](C([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1)=O)[C:16]([OH:18])=[O:17])(O)=O.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[OH2:34].[CH:35]1[CH:40]=CC=CC=1>>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[CH:40][C:35]([NH:28][C:33]2[C:15](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:16]([O-:18])=[O:17])=[O:34])=[CH:4][C:5]=1[O:6][CH3:7].[NH2+:21]1[CH2:22][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 1183VanillinHCID 8082PiperidineHCID 20222317HCID 20222317, compound

Product 1

HCID 178420620HCID 178420620, compoundYield 94.7%

Procedure

A solution of 2.54 g of vanillin, 3.8 g of 2-carboxymalonanilic acid, and 14.3 g of piperidine in 20 ml of benzene is heated for 3 hours under reflux with removal of water of reaction. After completion of the reaction, the reaction mixture is cooled and the precipitated crystals are collected by filtration and dried to obtain 6.3 g of piperidinium N-(4-hydroxy-3-methoxycinnamoyl)anthranilate (94.7% yield), m.p. 188°-189° C. The compound structure is confirmed by elemental analysis, and by IR and NMR spectroscopy.

Workup

  1. customAfter 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-8714a14d4ba343d5b3a7b99cf52a3071
Source dataset
uspto-grants-1986_11
Patent number
US04623724

Reaction notes

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