Hydrochloric Acid → HCID 53816044, compound

HRID 279966Notes

Reaction equation

HRID 279966 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]=[CH:7][C:8]([NH:10][C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]([O-:15])=[O:14])=[O:9])=[CH:4][C:3]=1[O:22][CH3:23].[NH2+]1CCCCC1.Cl>O.CO>[OH:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]=[CH:7][C:8]([NH:10][C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[O:9])=[CH:4][C:3]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178420620HCID 178420620, compound

Product 1

HCID 53816044HCID 53816044, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 10 g quantity of piperidinium N-(4-hydroxy-3-methoxycinnamoyl)anthranilate is dissolved in a mixture of 80 ml of water and 60 ml of methyl alcohol with heating, and the resultant solution is added dropwise to 85 ml of diluted hydrochloric acid (5 ml of conc. hydrochloric acid and 80 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 N-(4-hydroxy-3-methoxycinnamoyl)anthranilic acid (98.5% yield), m.p. 230°-233° 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-34b88580bc684454ba03e36fdf4ff931
Source dataset
uspto-grants-1986_05
Patent number
US04587356

Reaction notes

Loading…