Nitrosobenzene → N-hydroxy-N-phenylcyclopropanecarboxamide

HRID 1099335

Reaction equation

HRID 1099335 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12]1([CH:15]=[O:16])[CH2:14][CH2:13]1.[N:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]>ClCCl>[OH:18][N:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([CH:12]1[CH2:14][CH2:13]1)=[O:16]

Participants

5

Reactant 3

HCID 11473NitrosobenzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123114Cyclopropanecarboxaldehyde

Product 1

HCID 24938705N-hydroxy-N-phenylcyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of cyclopropanal (70 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-9adaf506175c49d68e38d70446ff1402
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Linked notes

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