Hydroxylamine → 2-chloro-N'-hydroxy-4-pyridinecarboximidamide

HRID 450631Notes

Reaction equation

HRID 450631 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[NH2:10][OH:11]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5](=[N:10][OH:11])[NH2:6]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 1359155502-chloro-N'-hydroxy-4-pyridinecarboximidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloroisonicotinonitrile (Aldrich, 0.73 g, 5.27 mmol), and hydroxylamine (Aldrich, 50 wt %, 0.348 g, 5.27 mmol) in methanol (10 mL) was heated to reflux and stirred for 1 hour. The volatiles were removed under reduced pressure to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 6.09 (s, 2 H), 7.67 (dd, J=5.4, 1.4 Hz, 1H), 7.73 (d, J=2.0 Hz, 1 H), 8.40 (d, J=5.2 Hz, 1 H), 10.22 (s, 1 H) ppm; MS (DCI/NH3) m/z 172 (M+H)+, 174 (M+H)+.

Workup

  1. temperatureto reflux
  2. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-13de78a8cbcd4264836a5dbc3503c5d6
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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