2-Amino-5-chlorobenzoic acid → N-(3,4-dimethoxycinnamoyl)-5-chloroanthranilic acid

HRID 1156853

Reaction equation

HRID 1156853 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:17]=[CH:18][C:19](Cl)=[O:20]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:17]=[CH:18][C:19]([NH:11][C:5]1[C:6](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:7]([OH:9])=[O:8])=[O:20]

Participants

5

Reactant 2

HCID 124762-Amino-5-chlorobenzoic acidHCID 533992063,4-Dimethoxycinnamoylchloride

Product 1

HCID 54036349N-(3,4-dimethoxycinnamoyl)-5-chloroanthranilic acidYield 43.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

In a mixture of 30 ml of chloroform and 3 ml of triethylamine is dissolved 3.4 g of 5-chloroanthranilic acid. To this solution is added a solution of 4.5 g of 3,4-dimethoxycinnamoylchloride in chloroform, and the mixture is heated under reflux for 2 hours. The reaction mixture is concentrated under a reduced pressure, and to the residue is added water and hydrochloric acid then added to make the mixture weakly acidic. The precipitated crystals are collected by filtration and recrystallized from ethanol to obtain 3.1 g of N-(3,4-dimethoxycinnamoyl)-5-chloroanthranilic acid as pale yellow needles.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture is concentrated under a reduced pressure
  4. additionto the residue is added water and hydrochloric acid
  5. additionthen added
  6. filtrationThe precipitated crystals are collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c73fa068b6df462781de51a9b738a5a4
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Linked notes

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