Water → p-((1-Oxoallyl)amino)benzoic acid

HRID 2042752Notes

Reaction equation

HRID 2042752 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].O>CN(C=O)C.N1C=CC=CC=1>[C:11]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:14])[CH:12]=[CH2:13]

Participants

6

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 13140Acryloyl chloride

Product 1

HCID 84866p-((1-Oxoallyl)amino)benzoic acidYield 94.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-aminobenzoic acid (1.40 g, 10 mmol) in DMF (10 mL) and pyridine (0.5 ml) was cooled to 0° C. To this solution was added of acryloyl chloride (0.94 g, 10 mmol) and the resulting mixture was stirred for 3 hours. The mixture was poured into 200 ml of water and the white solid obtained was filtered, washed with water and ether. Drying under high vacuum provided 1.8 g of the desired product which was used in the next step without purification.

Workup

  1. customthe white solid obtained
  2. filtrationwas filtered
  3. washwashed with water and ether
  4. customDrying under high vacuum

Sources & evidence

ORD record
ord-110f2d321652468f97d23fe6114139f4
Source dataset
uspto-grants-2013_11
Patent number
US08586600B2

Reaction notes

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