Hydrochloric Acid → N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilic acid

HRID 1156855Notes

Reaction equation

HRID 1156855 reaction equation
[OH-].[Na+].C(O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:11]([NH:13][C:14]1[C:15](=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:16]([O:18]C)=[O:17])=[O:12].Cl>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:11]([NH:13][C:14]1[C:15](=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:16]([OH:18])=[O:17])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 12852881methyl N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilate

Product 1

HCID 12852880N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilic acidYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 20 ml of a 10% aqueous solution of sodium hydroxide and 10 ml of ethanol is added 0.95 g of methyl N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilate and the mixture is stirred at room temperature for 1 hour. The reaction mixture is poured into 100 ml of water and after cooling, hydrochloric acid is added to make the mixture weakly acidic. The precipitated crystals are collected by filtration and recrystallized from ethanol to obtain 0.7 g of N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilic acid as colorless needles.

Workup

  1. temperatureafter cooling
  2. filtrationThe precipitated crystals are collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ca415bc9bf2f4638b37f464c410206a9
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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