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

HRID 2225314Notes

Reaction equation

HRID 2225314 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-a392c6df74414db68e6dc8b1045d7bcf
Source dataset
uspto-grants-1994_09
Patent number
USRE034722

Reaction notes

Loading…