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

HRID 1153882Notes

Reaction equation

HRID 1153882 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-859d77f5e83a481592deb5243f6c1756
Source dataset
uspto-grants-1984_12
Patent number
US04486597

Reaction notes

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