Triethylamine → HCID 54035979, compound

HRID 1156857Notes

Reaction equation

HRID 1156857 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].[CH3:23][C:24]1[CH:32]=[C:28]([C:29]([OH:31])=[O:30])[C:27]([NH2:33])=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[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:27]1[C:28](=[CH:32][C:24]([CH3:23])=[CH:25][CH:26]=1)[C:29]([OH:31])=[O:30])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 762552-Amino-5-methylbenzoic acidHCID 533992063,4-Dimethoxycinnamoylchloride

Product 1

HCID 54035979HCID 54035979, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In a mixture of 3 g of 5-methylanthranilic acid in 30 ml of chloroform is dissolved 3 ml of triethylamine, to this mixture is added a solution of 4.2 g of 3,4-dimethoxycinnamoylchloride in chloroform under cooling. The mixture is stirred at room temperature for 2 hours and then heated under reflux for 2 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 recrystallized from ethanol to obtain 4.8 g of N-(3,4-dimethoxycinnamoyl)-5-methylanthranilic acid as pale yellow needles.

Workup

  1. temperatureunder cooling
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. concentrationThe reaction mixture is concentrated under a reduced pressure, to the residue
  5. additionis added water and hydrochloric acid
  6. additionis added
  7. filtrationThe precipitated crystals are collected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-69d54451305142ccbc3845cb5bbb764c
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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