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

HRID 358485

Reaction equation

HRID 358485 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]>C(OCC)C>[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

Conditions

Temperature
40 °C

Procedure

100 Grams of m-aminobenzoic acid was suspended in 1 liter of diethyl ether, and at a room temperature with stirring 44.6 g of β-ethoxyacrylic chloride was added dropwise. Then the reaction mixture was heated at 40° C. for 5 hours. After the reaction was completed, the precipitated matter was collected by filtration and washed with water three times, and dried, and recrystallized from methanol to obtain 60 g of m-carboxy-N-(β-ethoxyacryloyl)aniline. Colorless cotton-like crystals. Melting point: 200.5°-202° C.

Workup

  1. additionwas added dropwise
  2. filtrationthe precipitated matter was collected by filtration
  3. washwashed with water three times
  4. customdried
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-82ac0c8bc46149e89cfcb0ab00532117
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Linked notes

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