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

HRID 1731874Notes

Reaction equation

HRID 1731874 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+]1CCOCC1.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 70467859HCID 70467859, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 20 g quantity of morpholinium N-(3,4-dimethoxycinnamoyl)anthranilate is dissolved in 40 ml of water and the resultant 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% yield). The compound is confirmed as identical to that obtained in EXAMPLE VI.

Workup

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

Sources & evidence

ORD record
ord-032a9fe8ab014425bb0d03bd85f72986
Source dataset
uspto-grants-1986_11
Patent number
US04623724

Reaction notes

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