Benzaldehyde → N-hydroxy-N-o-tolylbenzamide

HRID 1099346Notes

Reaction equation

HRID 1099346 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]=[O:28]>ClCCl>[OH:28][N:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH3:20])[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 119092-NitrosotolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 11320141N-hydroxy-N-o-tolylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of benzaldehyde (106 mg, 1 mmol), 1-methyl-2-nitrosobenzene (121 mg, 1 mmol) and catalyst (36.4 mg, 0.1 mmol) in dichloromethane (5 ml). The reaction mixture was stirred at room temperature for 60 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-e23d33c88e1a4b4daeef60ef87dc7582
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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