Triethylamine → N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilic acid

HRID 1156858Notes

Reaction equation

HRID 1156858 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15](Cl)=[O:16].[Cl:23][C:24]1[CH:25]=[C:26]([NH2:33])[C:27](=[CH:31][CH:32]=1)[C:28]([OH:30])=[O:29]>O1CCCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15]([NH:33][C:26]1[C:27](=[CH:31][CH:32]=[C:24]([Cl:23])[CH:25]=1)[C:28]([OH:30])=[O:29])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666462-Amino-4-chlorobenzoic acidHCID 533992063,4-Dimethoxycinnamoylchloride

Product 1

HCID 54481802N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a mixture of 3.4 g of 4-chloroanthranilic acid in 50 ml of tetrahydrofuran is dissolved 3 ml of triethylamine, to this mixture is added slowly a solution of 4.5 g of 3,4-dimethoxycinnamoylchloride in tetrahydrofuran under room temperature, and this solution is stirred at room temperature for 5 hours. The reaction mixture is concentrated under a reduced pressure, to the residue is added water and hydrochloric acid is added to make the mixture the weakly acidic. The precipitated crystals are collected by filtration and recrystallized from a mixture of dimethylformamide and water to obtain 5.9 g of N-(3,4-dimethoxycinnamoyl)-4-chloroanthranilic acid as colorless prisms.

Workup

  1. concentrationThe reaction mixture is concentrated under a reduced pressure, to the residue
  2. additionis added water and hydrochloric acid
  3. additionis added
  4. filtrationThe precipitated crystals are collected by filtration
  5. customrecrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-dce3bd7a4ee6444f9b8e78513c842fe9
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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