Benzene → HCID 178420620, compound

HRID 1153880Notes

Reaction equation

HRID 1153880 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 1.43 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-dea76c8bbd41456381667181ef7b5798
Source dataset
uspto-grants-1984_12
Patent number
US04486597

Reaction notes

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