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

HRID 2178185

Reaction equation

HRID 2178185 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-8471144d668d4d5e888fb6ff29bf7a75
Source dataset
uspto-grants-2015_06
Patent number
US09067929B2

Linked notes

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