Triethylamine → methyl N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilate

HRID 1156854Notes

Reaction equation

HRID 1156854 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([NH2:12])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19].C(N(CC)CC)C>O1CCCC1>[CH3:27][O:26][C:22]1[CH:21]=[C:17]([CH:16]=[C:15]([O:14][CH3:13])[C:23]=1[O:24][CH3:25])[C:18]([NH:12][C:5]1[C:6](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 78878Methyl 2-amino-5-chlorobenzoate

Product 1

HCID 12852881methyl N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilateYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.3 g of methyl 5-chloroanthranilate and 1.8 g of 3,4,5-trimethoxybenzoylchloride in 30 ml of tetrahydrofuran is added 1.5 g of triethylamine under cooling, and the mixture is stirred at room temperature for 2 hours and then heated under reflux for 1 hour. The reaction mixture is concentrated under reduced pressure and to the residue is added water. The precipitated crystals are collected by filtration and recrystallized from a mixture of chloroform and ether to obtain 1.4 g of methyl N-(3,4,5-trimethoxybenzoyl)-5-chloroanthranilate as colorless prisms.

Workup

  1. temperatureunder cooling
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. concentrationThe reaction mixture is concentrated under reduced pressure and to the residue
  5. additionis added water
  6. filtrationThe precipitated crystals are collected by filtration
  7. customrecrystallized from a mixture of chloroform and ether

Sources & evidence

ORD record
ord-bbe189cfd4084886aeb9bfcdbb6ed370
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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