Benzene → HCID 178420620, compound

HRID 279965Notes

Reaction equation

HRID 279965 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].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:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[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:3]=1[O:10][CH3:11].[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, compound

Procedure

A solution of 2.54 g of 4-hydroxy-3-methoxybenzaldehyde, 3.8 g of 2-carboxymalonanilic acid, and 4.29 g of piperidine in 17 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 6.34 g of piperidinium N-(4-hydroxy-3-methoxycinnamoyl)anthranilate, mp. 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-0ec806ee364941769c7d9ffb4a9afac1
Source dataset
uspto-grants-1986_05
Patent number
US04587356

Reaction notes

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