Hydrochloric Acid → N-(3′,4′-Dimethoxycinnamoyl)anthranilic acid

HRID 1731873Notes

Reaction equation

HRID 1731873 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:6]=[CH:7][C:8]([NH:10][C:11]1[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:13]([O-:15])=[O:14])=[O:9].[NH2+]1CCCCC1.Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:6]=[CH:7][C:8]([NH:10][C:11]1[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:13]([OH:15])=[O:14])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70467484HCID 70467484, compound

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 20 g of quantity of piperidinium N-(3,4-dimethoxycinnamoyl)anthranilate is dissolved in 60 ml of water with heating, and the resultant aqueous solution is added dropwise to 45 ml of diluted hydrochloric acid (5 ml of conc. hydrochloric acid and 40 ml of water) with stirring. The precipitated crystals which form are collected by filtration, washed with water and then dried at 90°-100° C. under reduced pressure for 3 hours to yield 15.5 g of N-(3,4-dimethoxycinnamoyl)anthranilic acid (98.0% yield), m.p. 208°-208.5° C. The compound structure is confirmed by elemental analysis, and by IR and NMR spectroscopy.

Workup

  1. temperaturewith heating
  2. filtrationThe precipitated crystals which form are collected by filtration
  3. washwashed with water
  4. customdried at 90°-100° C. under reduced pressure for 3 hours

Sources & evidence

ORD record
ord-95b5d42e70cb44a3b4176483a19efbd7
Source dataset
uspto-grants-1986_11
Patent number
US04623724

Reaction notes

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