Water → N-(2-Hydroxyphenyl)prop-2-enamide

HRID 547241Notes

Reaction equation

HRID 547241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Cl-].[Li+].[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].O>CN1CCCC1=O>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:11](=[O:14])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 58012-AminophenolHCID 13140Acryloyl chlorideHCID 433294Lithium Chloride2×

Product 1

HCID 12998435N-(2-Hydroxyphenyl)prop-2-enamideYield 34.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

20 g of o-amino phenol was dissolved in 200 mL of N-methyl-2-pyrrolidone (NMP), and then the solution was ice-cooled. To the solution was added 8.546 g (1.1 times in mol) of lithium chloride. After lithium chloride was entirely dissolved, 17.42 g (1.05 times in mol) of acryloyl chloride was dropped into the solution, and the solution was stirred under ice-cooling for 5 hours. The reaction mixture was poured into 1.8 L of water, and an organic layer was extracted with 700 mL of diethyl ether. The diethyl ether layer was sequentially washed with 0.2 N hydrochloric acid, brine and water, and dried over magnesium sulfate. Diethyl ether was evaporated off under a reduced pressure. 80 mL of diisopropyl ether was added to the solidified residue, and the solution was heated and stirred to wash and filter the residue. The same washing process was carried out once again to obtain 10.2 g of N-(2-hydroxyphenyl)acrylamide as white powder (yield: 34%).

Workup

  1. temperaturecooled
  2. temperaturecooling for 5 hours
  3. extractionan organic layer was extracted with 700 mL of diethyl ether
  4. washThe diethyl ether layer was sequentially washed with 0.2 N hydrochloric acid, brine and water
  5. dry with materialdried over magnesium sulfate
  6. customDiethyl ether was evaporated off under a reduced pressure
  7. addition80 mL of diisopropyl ether was added to the solidified residue
  8. temperaturethe solution was heated
  9. stirringstirred
  10. washto wash
  11. filtrationfilter the residue

Sources & evidence

ORD record
ord-2ee07a63cd8e4fee96110535f49b8c54
Source dataset
uspto-grants-2011_05
Patent number
US07939241B2

Reaction notes

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