N-Phenylhydroxylamine → HCID 86631008, compound

HRID 600375Notes

Reaction equation

HRID 600375 reaction equation
[C:1]1([NH:7][OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9](=O)/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[C:12]1(/[CH:11]=[CH:10]/[CH:9]=[N+:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O-:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7518N-PhenylhydroxylamineHCID 637511Cinnamaldehyde

Product 1

HCID 86631008HCID 86631008, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

According to the literature procedure (Utzinger et al. Helv. Chim. Acta 1954, 37, 1892; incorporated herein by reference) N-phenyl-hydroxylamine (188.7 mg, 1.7 mmol, 1.0 equiv) was added to a solution of (E)-cinnamaldehyde (218 μL, 1.73 mmol, 1 equiv) in ethanol (1.5 mL, absolute). The bright yellow solution was stirred for 9 h at 23° C. in the dark, and then was cooled in an ice bath. The cooled, heterogeneous solution was filtered and the filter cake was washed once with hexanes (10 mL). The filter cake was dried in vacuo overnight, furnishing α-(trans-2-phenyl-ethenyl)-N-phenylnitrone (293 mg, 76%, yellow solid) mp=150-152° C. (lit. 150-151° C.). 1H NMR data were in accord with that previously reported.

Workup

  1. temperaturethen was cooled in an ice bath
  2. filtrationThe cooled, heterogeneous solution was filtered
  3. washthe filter cake was washed once with hexanes (10 mL)
  4. customThe filter cake was dried in vacuo overnight

Sources & evidence

ORD record
ord-aadda8dc7052487999593001522efd67
Source dataset
uspto-grants-2011_03
Patent number
US07902196B2

Reaction notes

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