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

HRID 1153881Notes

Reaction equation

HRID 1153881 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 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-0bf6d580b64443118eab13e6ca77d932
Source dataset
uspto-grants-1984_12
Patent number
US04486597

Reaction notes

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