Hydroxylamine → N'-hydroxy-4-phenoxybenzenecarboximidamide

HRID 2167321Notes

Reaction equation

HRID 2167321 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][OH:17]>C(O)C>[OH:17]/[N:16]=[C:12](\[NH2:13])/[C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 1378214-Phenoxybenzonitrile

Product 1

HCID 21226048N'-hydroxy-4-phenoxybenzenecarboximidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (5.0 mL), was combined 4-phenoxybenzonitrile (200 mg, 1.02 mmol) and hydroxylamine (250 μL, 4.09 mmol). The mixture was refluxed for 3 hours. The reaction was cooled and then concentrated in vacuo to give the product, which was taken to the next step without further purification (quantitative yield). 1H NMR (500 MHz, CDCL3) δ(ppm): 4.87 (2H, bs), 7.01 (2H, d, J=9.0 Hz), 7.03 (2H, dd, J=8.7, 1.1 Hz), 7.15 (2H, tt, J=7.4, 1.1 Hz), 7.36 (2H, dd, J=8.6, 7.3 Hz), 7.59 (2H, d, J=9.0 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 118.6 (CH), 119.6 (CH), 124, 127.3, 127.6 (CH), 130.1 (CH), 152.5, 156.6, 159.3. MS (FAB+): 229 (MH+). HRMS for C13H12N2O2 (MH+): calculated: 229.0977; found 229.0977.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. customto give the product, which
  5. customwas taken to the next step without further purification (quantitative yield)

Sources & evidence

ORD record
ord-bf520b9f38b24a71b75689ad644ebcdd
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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