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

HRID 1156852Notes

Reaction equation

HRID 1156852 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:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18]>N1C=CC=CC=1.O1CCCC1>[CH3:26][O:25][C:21]1[CH:20]=[C:16]([CH:15]=[C:14]([O:13][CH3:12])[C:22]=1[O:23][CH3:24])[C:17]([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:18]

Participants

5

Reactant 2

HCID 124762-Amino-5-chlorobenzoic acidHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Product 1

HCID 12852880N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilic acidYield 38.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.7 g of 5-chloroanthranilic acid in 40 ml of pyridine is added a solution of 2.6 g of 3,4,5-trimethoxybenzoylchloride in tetrahydrofuran under cooling, and the mixture is stirred at room temperature for 2 hours and then heated to 80° C. for 30 minutes. The reaction mixture is concentrated under a reduced pressure and to the residue is added water. The precipitated crystals are recrystallized from acetone to obtain 1.4 g of N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilic acid as colorless needles.

Workup

  1. temperatureunder cooling
  2. temperatureheated to 80° C. for 30 minutes
  3. concentrationThe reaction mixture is concentrated under a reduced pressure and to the residue
  4. additionis added water
  5. customThe precipitated crystals are recrystallized from acetone

Sources & evidence

ORD record
ord-509a9a36b5a441688650374d351861fa
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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