Acrolein → N-hydroxy-N-phenylacrylamide

HRID 1099342Notes

Reaction equation

HRID 1099342 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12]([CH:14]=[CH2:15])=[O:13].[N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>ClCCl>[OH:17][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12](=[O:13])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 7847AcroleinHCID 11473NitrosobenzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 11367183N-hydroxy-N-phenylacrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of acrolein (56 mg, 1 mmol), nitrosobenzene (107 mg, 1 mmol) and catalyst (36.4 mg, 0.1 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed under vacuum, and the residue was purified by flash silica gel column chromatography using hexane and ethyl acetate as the eluents.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-e7d3fe7446df43ba98b638eb2281a540
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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