Hydrochloric Acid → HCID 53664003, compound

HRID 279968Notes

Reaction equation

HRID 279968 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:5]=[CH:6][C:7]([NH:9][C:10]1[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:12]([O-:14])=[O:13])=[O:8].[NH2+]1CCCCC1.Cl>O.CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:5]=[CH:6][C:7]([NH:9][C:10]1[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:12]([OH:14])=[O:13])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178420619HCID 178420619, compound

Product 1

HCID 53664003HCID 53664003, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 10 g quantity of piperidinium N-(3-hydroxy-4-methoxycinnamoyl)anthranilate is dissolved in a mixture of 80 ml of water and 80 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-(3-hydroxy-4-methoxycinnamoyl)anthranilic acid (97.0% yield), m.p. 219°-222° 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-101a9159eef54c8c9bd310d0635e5369
Source dataset
uspto-grants-1986_05
Patent number
US04587356

Reaction notes

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