3-Aminobenzoic Acid → HCID 54034085, compound

HRID 1904163Notes

Reaction equation

HRID 1904163 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([OH:10])=O.C(Cl)(=O)OCC.[NH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=[O:27]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([NH:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=[O:27])=[O:10]

Participants

6

Reactant 3

HCID 74193-Aminobenzoic AcidHCID 10928Ethyl chloroformateHCID 168483',4'-Dimethoxycinnamic acid

Product 1

HCID 54034085HCID 54034085, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

2 Grams of 3,4-dimethoxycinnamic acid were dissolved in a mixture of 20 ml of dry dimethylformamide and 1.5 g of triethylamine. To this solution was added under ice cooling and agitation 1.1 g of ethyl chlorocarbonate and the mixture was then reacted for one hour. To this mixture were added 10 ml of dimethylformamide containing 1.5 g of 3-aminobenzoic acid and the mixture was stirred for 2 hours. After completion of the reaction, the reaction liquid was concentrated approximately to 1/2 volume and poured into an aqueous solution of hydrochloric acid. The precipitated crystals were separated by filtration, washed with water and recrystallized from an equivolume mixture of ethanol and water to obtain a yield of 50% 3-(3',4'-dimethoxycinnamoylamino)-benzoic acid having a melting point of 225°-226° C.

Workup

  1. additionTo this solution was added under ice cooling
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. concentrationwas concentrated approximately to 1/2 volume
  5. additionpoured into an aqueous solution of hydrochloric acid
  6. customThe precipitated crystals were separated by filtration
  7. washwashed with water
  8. customrecrystallized from an equivolume mixture of ethanol and water

Sources & evidence

ORD record
ord-40251adf5f844cb3b4e62efcac4d27af
Source dataset
uspto-grants-1989_06
Patent number
USRE032944

Reaction notes

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