Hydroxylamine → HCID 43188223, compound

HRID 2167330Notes

Reaction equation

HRID 2167330 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[NH2:18][OH:19]>C(O)C>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11](/[C:12](/[NH2:13])=[N:18]/[OH:19])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 14902794-(4-methoxyphenoxy)benzonitrile

Product 1

HCID 43188223HCID 43188223, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4-Methoxyphenoxy)benzonitrile (581 mg, 2.58 mmol) was dissolved in ethanol (10.0 mL) and hydroxylamine (630 μL, 10.32 mmol) was added. The mixture was refluxed for 1 hour and the reaction was cooled and then concentrated in vacuo to give the crude product which was taken to the next step without further purification (636 mg, 95%). 1H NMR (500 MHz, CDCL3) δ(ppm): 3.81 (1H, s), 4.87 (1H, bs), 6.88-6.94 (4H, m), 6.99 (2H, d, J=9.2 Hz), 7.55 (2H, d, J=9.0 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 55.8 (CH3), 115.2 (CH), 117.4 (CH), 121.4 (CH), 126.6 (CH), 127.6, 149.5, 152.5, 156.5, 160.4. MS (FAB+): 259 (MH+). HRMS for C14H14N2O3 (MH+): calculated: 259.1083; found 259.1100.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperaturethe reaction was cooled
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-816c655a2da7494698c8b72e760aad8b
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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