Hydroxylamine → HCID 59533948, compound

HRID 2167342Notes

Reaction equation

HRID 2167342 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:3][CH:2]=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:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 57390371HCID 57390371, compound

Product 1

HCID 59533948HCID 59533948, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Pyridin-4-yloxy)benzonitrile (293 mg, 1.49 mmol) was dissolved in ethanol (6.0 mL) and hydroxylamine (197 mg, 5.97 mmol) was added. The mixture was refluxed for 3 hours and cooled to room temperature and then concentrated in vacuo to give the product which immediately formed white crystals and was taken to the next step without further purification. A small quantity was purified by column chromatography (Hex/EtOAc 1:8) to give the pure product (323 mg, 94%). 1H NMR (500 MHz, DMSO-d6) δ(ppm): 5.95 (2H, s), 6.24 (2H, d, J=8.0 Hz), 7.56 (2H, d, J=8.8 Hz), 7.84 (2H, d, J=8.6 Hz), 8.02 (2H, d, J=7.8 Hz), 9.81 (1H, s). 13C NMR (125 MHz, DMSO-d6) δ(ppm): 118.0 (CH), 122.1 (CH), 126.7 (CH), 132.6, 139.6 (CH), 142.8, 149.8, 177.4. MS (FAB+): 230 (MH+). HRMS for C12H11N3O2 (MH+): calculated: 230.0930; found 230.0950.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. concentrationconcentrated in vacuo
  3. customto give the product which immediately formed white crystals
  4. customwas taken to the next step without further purification
  5. customA small quantity was purified by column chromatography (Hex/EtOAc 1:8)

Sources & evidence

ORD record
ord-95024e05cfca44fcb11c2d638f66b96c
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

Loading…