Hydroxylamine → HCID 59533941, compound

HRID 2167334Notes

Reaction equation

HRID 2167334 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=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:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 185258324-[(Pyridin-2-yl)oxy]benzonitrile

Product 1

HCID 59533941HCID 59533941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Pyridin-2-yloxy)benzonitrile (701 mg, 3.57 mmol) was dissolved in ethanol (14.0 mL), and hydroxylamine (472 mg, 14.3 mmol) was added and the mixture was refluxed for 16 hours. The reaction was cooled to room temperature and then concentrated in vacuo to give the product as a yellow syrup and was taken to the next step without further purification (818 mg, 100%). 1H NMR (500 MHz, CDCL3) δ(ppm): 4.91 (2H, bs), 6.94 (1H, dt, J=8.4, 0.8 Hz), 7.02 (1H, ddd, J=7.2, 5.0, 0.8 Hz), 7.16 (2H, d, J=8.6 Hz), 7.66 (2H, d, J=8.6 Hz), 7.71 (1H, ddd, J=8.2, 7.2, 2.0 Hz), 8.21 (1H, ddd, J=5.0, 2.0, 0.8 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 112.1 (CH), 119.1 (CH), 121.4 (CH), 127.6 (CH), 129.0, 139.8 (CH), 147.9 (CH), 152.4, 155.8, 163.4. MS (FAB+): 230 (MH+). HRMS for C12H11N3O2 (MH+): calculated: 230.0930; found 230.0934.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05c5a7f94b12490181955175429d7166
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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