Hydroxylamine → N-hydroxy-4-methoxybenzenecarboximidamide

HRID 2167327Notes

Reaction equation

HRID 2167327 reaction equation
[C:1](#[N:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH2:11][OH:12]>C(O)C>[OH:12]/[N:11]=[C:1](\[NH2:10])/[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 701294-Methoxybenzonitrile

Product 1

HCID 5360053N-hydroxy-4-methoxybenzenecarboximidamideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of anisonitrile (300 mg, 2.25 mmol) and hydroxylamine (275 μL, 9.01 mmol) in ethanol (5.0 mL) was refluxed for 3 hours. The reaction was cooled and then concentrated in vacuo to give the product (370 mg, 99%), which immediately formed white crystals and was taken to the next step without further purification. A small quantity was purified by column chromatography over silica gel (Hex/EtOAc 1:8) to give the product (370 mg, 99%) as a white solid. 1H NMR (500 MHz, CDCL3) δ(ppm): 3.83 (3H, s), 4.86 (2H, bs), 6.91 (2H, d, J=8.4 Hz), 7.56 (2H, d, J=8.4 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 55.5 (CH3), 114.2 (CH), 125.1, 127.4 (CH), 152.7, 161.2. MS (FAB+): 167 (MH+). HRMS for O8H10N2O2 (MH+): calculated: 167.0821; found 167.0803.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd6357b85ceb41fca4215ed73c058009
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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