Hydroxylamine → 3-Cyano-N-hydroxy-benzamidine

HRID 450592Notes

Reaction equation

HRID 450592 reaction equation
[NH2:1][OH:2].[OH-].[Na+].[C:5](#[N:14])[C:6]1[CH:13]=[CH:12][CH:11]=[C:8]([C:9]#[N:10])[CH:7]=1>C(O)C>[C:9]([C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[C:5](=[N:1][OH:2])[NH2:14])#[N:10]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 12276IsophthalonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 573689333-Cyano-N-hydroxy-benzamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydroxylamine (Aldrich, 7.65 g, 100 mmol) in ethanol (100 mL) was treated with 10 N NaOH (10 mL, 100 mmol). To this solution, isophthalonitrile (Aldrich, 12.8 g, 100 mmol) in 100 mL of ethanol was added. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed under vacuum and the residue was purified with flash column chromatography (5% methanol/dichloromethane) to give the titled product. 1H NMR (300 MHz, DMSO-d6) δ 5.98 (bs, 2 H), 7.59 (t, J=7.4 Hz, 1 H), 8.06-8.0 (m, 2 H), 9.89 (s, 1 H) ppm; MS (DCI/NH3) m/z 162 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified with flash column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ccf0ba8868db47acb177d2936d7713a8
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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