Sodium Hydroxide → sodium N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilate

HRID 1156860Notes

Reaction equation

HRID 1156860 reaction equation
[OH-].[Na+:2].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:8]=[CH:9][C:10]([NH:12][C:13]1[C:14](=[CH:18][CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:15]([OH:17])=[O:16])=[O:11]>>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:8]=[CH:9][C:10]([NH:12][C:13]1[C:14](=[CH:18][CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:15]([O-:17])=[O:16])=[O:11].[Na+:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54481802N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilic acid

Product 1

HCID 70541710sodium N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilateYield 83.8%

Procedure

In 300 ml of an aqueous alcoholic solution (ethanol 1:water 1) containing 0.4 g of sodium hydroxide is added 3.6 g of N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilic acid and the mixture is warmed to be completely dissolved. The solution is concentrated under a reduced pressure, the residue is dissolved in 200 ml of warmed ethanol and to this solution is added 900 ml of ether. The precipitated crystals are collected by filtration and dried under reduced pressure to obtain 3.2 g of sodium N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilate.

Workup

  1. temperaturethe mixture is warmed
  2. dissolutionto be completely dissolved
  3. concentrationThe solution is concentrated under a reduced pressure
  4. dissolutionthe residue is dissolved in 200 ml of warmed ethanol and to this solution
  5. additionis added 900 ml of ether
  6. filtrationThe precipitated crystals are collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-72c10026ca324256b03cc1fe68edad40
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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