3-Aminobenzoic Acid → 3-[(3-Ethoxyacryloyl)amino]benzoic acid

HRID 483150

Reaction equation

HRID 483150 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:11]([O:13][CH:14]=[CH:15][C:16](Cl)=[O:17])[CH3:12]>CCOCC>[C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[NH:1][C:16](=[O:17])[CH:15]=[CH:14][O:13][CH2:11][CH3:12])([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 30144293-Ethoxy-2-propenoyl chloride

Product 1

HCID 545354873-[(3-Ethoxyacryloyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

100 Grams of m-aminobenzoic acid was suspended in 1 liter of ether, then 44.6 g of β-ethoxyacrylyl chloride was added dropwise into the solution at a room temperature under stirring condition. This reaction mixture was kept at 40° C. for 5 hours, then the precipitate formed in the reaction mixture was collected by filtration. The crystals were washed with water three times, dried and recrystallized from methanol to obtain 60 g of m-carboxy-N-(β-ethoxyacryloyl)aniline in the form of colorless cotton-like crystals.

Workup

  1. customthe precipitate formed in the reaction mixture
  2. filtrationwas collected by filtration
  3. washThe crystals were washed with water three times
  4. customdried
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c9097c1091594a68afd2e5411c08ae4a
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Linked notes

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