4-Aminobenzoic Acid → p-((1-Oxoallyl)amino)benzoic acid

HRID 579725

Reaction equation

HRID 579725 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[NH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.Cl.NC1C=CC(C(O)=O)=CC=1>O1CCCC1>[C:1]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 13140Acryloyl chlorideHCID 12209225Aminobenzoic acid hydrochloride

Product 1

HCID 84866p-((1-Oxoallyl)amino)benzoic acidYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.66 g (7.3 mmoles) of acryloyl chloride was added to a solution of 2 g (14.3 mmoles) of p-aminobenzoic acid in 40 mL tetrahydrofuran (THF). A white precipitate consisting of p-aminobenzoic acid hydrochloride formed. The suspension was filtered and the filtrate was dried by vacuum evaporation to yield 1.1 g p-acrylamidobenzoic acid (reaction shown in FIG. 16a).

Workup

  1. customformed
  2. filtrationThe suspension was filtered
  3. customthe filtrate was dried by vacuum evaporation

Sources & evidence

ORD record
ord-bee312e1396e42e4aee42cf412906e72
Source dataset
uspto-grants-1988_06
Patent number
US04749647

Linked notes

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