4-Nitrobenzaldehyde → N-hydroxy-4-nitro-N-phenylbenzamide

HRID 1099329Notes

Reaction equation

HRID 1099329 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>ClCCl.C1CCN2C(=NCCC2)CC1>[OH:13][N:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 11473Nitrosobenzene

Product 1

HCID 4652094N-hydroxy-4-nitro-N-phenylbenzamideYield 96.8%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 6344DichloromethaneSolvent

Procedure

Scale up: DBU (3.8 mg, 0.025 mmol) was added under argon to a solution of 4-nitrobenzaldehyde (3 g, 20 mmol), nitrosobenzene (2.14 g, 20 mmol) and catalyst (9 mg, 0.025 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature for 2 min. The product precipitated as a yellow solid. The solvent was removed under vacuum, and the solid was washed with hexane and ether to yield a pure product (5 g).

Workup

  1. customThe product precipitated as a yellow solid
  2. customThe solvent was removed under vacuum
  3. washthe solid was washed with hexane and ether

Sources & evidence

ORD record
ord-e28ad15be0444bcba9c6840ee33a8b03
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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